Month: March 2021

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 30379-58-9, name is Benzyl 2-hydroxyacetate, molecular formula is C9H10O3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of Benzyl 2-hydroxyacetate

PREPARATION 42 N-{2-t-Butyl-5-[3-(benzyloxycarbonylmethoxycarbonyloxy)-4-cyclohexylbutyl]phenyl}-2-(9H-xanthen-9-yl)acetamide A solution of 55 mul (0.46 mmol) of trichloromethyl chloroformate in 1 ml of tetrahydrofuran was added dropwise to a solution of 74 mul (0.91 mmol) of pyridine in 1 ml of tetrahydrofuran, whilst ice-cooling, and then the temperature of the resulting mixture was allowed to rise gradually to room temperature. The mixture was stirred for 1 hour at room temperature, after which it was again cooled, and a solution of 400 mg (0.76 mmol) of N-[2-t-butyl-5-(4-cyclohexyl-3-hydroxybutyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 12) in 3 ml of tetrahydrofuran was added dropwise. The mixture was stirred for 1 hour at the same temperature, and then the solvent was removed by distillation under reduced pressure, to give a colorless foam-like material as a residue. This residue was dissolved in 1 ml of methylene chloride, and a solution of 151 mg (0.91 mmol) of benzyl alpha-hydroxyacetate in 1.5 ml of methylene chloride and then 110 mg (0.91 mmol) of 4-(N,N-dimethylamino)pyridine were added dropwise, whilst ice-cooling. The mixture was stirred at room temperature for 1 hour, and then the reaction mixture was diluted with methylene chloride, after which it was washed with water and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 75 g of silica gel, using a 1:9 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 522 mg (yield 96%) of the title compound as a colorless foam-like material. Infrared Absorption Spectrum (KBr) numax cm-1: 3274, 2924, 2853, 1750, 1655, 1480, 1458, 1422, 1256, 1194, 758.

With the rapid development of chemical substances, we look forward to future research findings about 30379-58-9.

Reference:
Patent; Sankyo Company, Limited; US5534529; (1996); A;,
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Reference of 98-55-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.98-55-5, name is 2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol, molecular formula is C10H18O, molecular weight is 154.25, as common compound, the synthetic route is as follows.

A method for preparing 1-p-menthene-8-thiol, comprising the steps of:S1, adding 1 kg of a-terpineol to the reaction vessel, adding 6 L of THF, and stirring until fully dissolved; S2, adding 1.44kg of phosphorus pentasulfide in portions to the solution obtained in step S1, heating up, and controlling temperature below 50 C; S3, reacting at 50 C for 1 hour, monitoring the GC in the gas phase, and the reaction is completed; S4, the reaction system is reduced to room temperature, rotary distillation to remove THF recovery, slowly adding 6L of 10% sodium hydroxide aqueous solution to pH ? 12; S5, extract the aqueous phase twice with a tertiary ether, 3L each time, The organic phase was combined and washed once with saturated brine for 1 L each time. Dry over anhydrous sodium sulfate and concentrate to give 1 kg crude. Distilled under reduced pressure to give 500 g of product 1-p-menthene-8-thiol. GC purity > 85%.

The chemical industry reduces the impact on the environment during synthesis 98-55-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shijiazhuang He Zhong Technology Co., Ltd.; Guo Junyong; Zhang Luanqing; Cao Yanlei; (9 pag.)CN109796385; (2019); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 68120-35-4, name is (3-Bromo-4-methylphenyl)methanol, the common compound, a new synthetic route is introduced below. Quality Control of (3-Bromo-4-methylphenyl)methanol

To a stirred solution of (3-bromo-4-methylphenyl) methanol (5.5 g, 27.4 mmol) in THF (50 mL) at -78C, n-BuLi [(18.6 g, 2.5 eq (2.5M soln) was added and the solution was stirred at same temperature for 30 mm. Then, 002 gas was purged (generated from dry ice) for about 10 mm. The reaction mixture was quenched with ammonium5 chloride and acidified with 1 N HCI, extracted with ethyl acetate, the organic layer was washed with water, brine solution. Then, it was dried over anhydrous Na2S04 and concentrated under reduced pressure and washed with n-hexane to obtain the title compound (4.0 g, 87.85%) as an off white solid. LCMS : 165.0 (M-H) 1H NMR:(CDCI3, 300MHz) 6 12.67 (5, 1H), 7.79 (5, 1H), 7.36-7.38 (d, 1H), 7.23-7.25 (d, 1H), 10 5.23 (5, 1H), 4.49 (5, 2H), 2.50 (5, 3H).

The synthetic route of 68120-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202528; (2014); A1;,
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Related Products of 931-17-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 931-17-9, name is 1,2-Cyclohexanediol. A new synthetic method of this compound is introduced below.

(Example 7a) Cyclopent-1-ene-1-carbaldehyde A mixture of sodium periodate (28.6 g, 134 mmol) and water (250 ml) was added to a mixture of 1,2-cyclohexanediol (12 g, 103 mmol) and diethyl ether (150 ml), which was stirred at room temperature for 35 minutes. A 20% aqueous potassium hydroxide solution (40 ml, 206 mmol) was added to the reaction mixture, which was stirred at room temperature for two hours. The reaction mixture was extracted with diethyl ether twice. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off to give the title compound (6.1 g, yield 61.6%). 1H-NMR (400 MHz, CDCl3) delta ppm; 1.96-2.04 (2H, m), 2.50-2.57 (2H, m), 2.58-2.66 (2H, m), 6.87-6.90 (1H, m), 9.80 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,931-17-9, 1,2-Cyclohexanediol, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; YOSHIDA Ichiro; OKABE Tadashi; MATSUMOTO Yasunobu; WATANABE Nobuhisa; OHASHI Yoshiaki; ONIZAWA Yuji; HARADA Hitoshi; EP2757103; (2014); A1;,
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Reference of 862135-61-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 862135-61-3, name is 5-Bromoindan-2-ol, molecular formula is C9H9BrO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A suspension of 5-bromoindan-2-ol (Combi-Blocks, cat No.QA3834: 114 mg, 0.535 mmol), potassium acetate (160 mg, 1.6 mmol) and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl](200 mg, 0.80 mmol) in 1,4-dioxane (2.4 mL) was first degassed with stream of nitrogen for ?5 min, then [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (20 mg, 0.03 mmol) was added and the mixture was heated to 100 C. overnight. The reaction mixture was cooled to room temperature, concentrated then diluted with 1:1 ethyl acetate/hexanes, filtered through celite, and concentrated. The residue obtained was purified by flash chromatography on a silica gel column eluting with 0 to 40% EtOAc/Hexanes to provide the desired intermediate in nearly quantitative yield.

According to the analysis of related databases, 862135-61-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Courter, Joel R.; He, Chunhong; Li, Jingwei; Lu, Liang; Sun, Yaping; Wang, Xiaozhao; Yao, Wenqing; Zhang, Colin; Zhuo, Jincong; (87 pag.)US2016/9720; (2016); A1;,
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Application of 17773-10-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 17773-10-3, name is Choline Iodide. This compound has unique chemical properties. The synthetic route is as follows.

CORM-338; [Me3NCH2CH2OH][Mn(CO)4I2]; 450 mg (1.40 mmol) of [Mn(CO)5I] and 301 mg (1.30 mmol) of choline iodide were stirred in 15 ml of methanol at 55 C. for 36 h. (The IR Spectrum recorded after 2 h showed a significant amount of starting material remained).Following this, the solvent was removed on a rotary evaporator to give a yellow/brown ?oily? solid. This residue was dissolved in DCM, filtered, and then diethyl ether added. This precipitated out a white solid (presumably unreacted choline iodide) which was filtered off. Solvent was then removed on a rotary evaporator and the residue again dissolved in DCM. A little hexane was then added. However, this resulted in the product separating as an oil. Hence all the solvent was removed on a rotary evaporator and the resulting semi-solid residue washed twice with diethyl ether. This produced a solid product that was dried under vacuum.405 mg (0.771 mmol) of an orange/brown solid was obtained. Mr=524.96.Yield was 59%.1H NMR (CD2Cl2): delta(ppm) 3.11 (br, OH 1H), 3.35 (br, CH3 9H), 3.68 (br, CH2 2H), 4.22 (br, CH2 2H)13O NMR (CD2Cl2): delta(ppm) 55.29 (t {J=3.9 Hz}, CH3), 56.35 (CH2), 68.16 (t {J=2.8 Hz}, CH2), 213.26 (CO), 221.91 (CO)17O NMR (CD2Cl2): delta(ppm) 377.3 (CO), 379.4 (CO)55Mn NMR (CD2Cl2): delta(ppm) -863 line width 6650 HzIR (CH2Cl2) nu(cm-1): 2077 (s), 2002 (vs), 1984 (s), 1942 (s)Mass Spec (m/z): 421 (MO), 393 (M–CO), 365 (M–2CO), 337 (M–3CO), 309 (M–4CO)Elemental: MnC9H14NO5I2 found (calc) C: 20.62 (20.59), H: 2.55 (2.69), N: 2.57 (2.67), I: 48.61 (48.35); CORM-369 (Choline][Mn(CO)4I2] [3]450 mg (1.40 mmol) of Mn(CO)5I and 301 mg (01.30 mmol) of choline iodide were stirred in 15 ml of methanol at 55 C. for 36 hrs. (IR recorded after 2 hrs showed a significant amount of starting material remaining).Following this, the solvent was removed on rotary evaporator to give a yellow/brown ?oily? solid. This residue was dissolved in DCM, filtered, and then ether added. This crashed out a white solid (presumably unreacted choline iodide) which was filtered off. Solvent was then removed on rotary evaporator and the residue again dissolved in DCM. A little hexane was then added. However, this resulted in the product crashing out as an oil. Hence all the solvent was removed on rotary evaporator and the resulting semi-solid residue washed twice with ether. This produced a solid product that was dried under vacuum.405 mg of an orange/brown solid was obtained. Yield was 59.3%.1H NMR (CD2Cl2): delta(ppm) 3.35 (br, NMe3), 3.69 (br, CH2), 4.18 (br, CH2)13C NMR (CD2Cl2): delta(ppm) 54.0 (NMe3), 56.6 (CH2), 68.5 (CH2), 211.6 (CO), 219.8 (CO),IR (CH2Cl2) nu(cm-1): 2092 (w), 2015 (vs), 1989 (s), 1943 (s)Mass Spec (m/z): 215 (M–4CO) (1:2:1 ratio of peaks observed, i.e. 79Br/81Br).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 17773-10-3, Choline Iodide.

Reference:
Patent; Motterlini, Roberto Angelo; Mann, Brian Ernest; Scapens, David Alistair; US2010/105770; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 100751-63-1, 6-Bromo-2-naphthylmethanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, SDS of cas: 100751-63-1, blongs to alcohols-buliding-blocks compound. SDS of cas: 100751-63-1

A mixture of the product from Example 1A (0.119 g, 0.50 mmol), 4 cyanophenylboronic acid (0.088 g, 0.60 mmol, 1.2 equiv.), PdCl2(PPh3)2 (7 mg, 0.001 mmol, 0.020 equiv.) and K3PO4H2O (288 mg, 1.5 mmol, 3.0 equiv.) in isopropanol (10 ML) and distilled water (4 ML) was stirred at 50 C. under a dry nitrogen atmosphere for 1.5 hr.The reaction mixture was cooled to room temperature then concentrated under reduced pressure.The residue was partitioned between ethyl acetate and saturated aqueous NH4Cl. The organic layer was dried (MgSO4), and filtered.The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (65:35 hexane/ethyl acetate).Fractions containing product were combined and concentrated under reduced pressure to provide the product as a white solid (95 mg, 73% yield). M.p. 174.1-175.5 C. 1H NMR (CDCl3, 300 MHz) delta 8.06 (d, J=2 Hz, 1H), 7.97-7.70 (m, 8H), 7.54 (dd, J=2, 12 Hz, 1H), 4.90 (dbr, J=6 Hz, 2H), 1.78 (tbr, J=6 Hz, 1H). MS (DCl-NH3) [M+NH4]+ at 277, [M+NH4 NH3]+ at 294.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100751-63-1, 6-Bromo-2-naphthylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-Jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Sharma, Padam N.; Bennani, Youssef L.; US2004/92521; (2004); A1;,
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Synthetic Route of 60666-70-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 60666-70-8, name is (2-Bromo-5-chlorophenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: A mixture of64(1.075g, 5.5mmol), 1-bromo-4-chlorobenzene (1.03g, 5.4mmol), Cs2CO3(2.28g, 7mmol) and BINAP (0.05 equiv) in toluene (60mL) was purged with N2, Pd(OAc)2(110mg, 0.22mmol) was added and the mixture was stirred under reflux for 16h, then cooled, diluted with EtOAc, filtered and evaporated. The residue was chromatographed on silica gel, with EtOAc/CH2Cl2(2:1) eluting24(0.62g. 37percent)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60666-70-8, (2-Bromo-5-chlorophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Flanagan, Jack U.; Atwell, Graham J.; Heinrich, Daniel M.; Brooke, Darby G.; Silva, Shevan; Rigoreau, Laurent J.M.; Trivier, Elisabeth; Turnbull, Andrew P.; Raynham, Tony; Jamieson, Stephen M.F.; Denny, William A.; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 967 – 977;,
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Electric Literature of 83647-43-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol. A new synthetic method of this compound is introduced below.

(2,3-dihydrobenzo[b][l,4]dioxin-6-yl)boronic acid (0.537 g, 2.98 mmol),(3- bromo-2-methylphenyl)methanol (0.5 g, 2.487 mmol) and 2nd Generation XPhos precatalyst (0.059 g, 0.075 mmol) was covered with THF (24 ml) and degassed. Potassium phosphate, tribasic (12.43 ml, 6.22 mmol) added as an 0.5 M aqueous solution. The reaction was stirred at room temperature sealed under argon overnight. The solvent was removed by rotary evaporation. The residue was purified using 3: 1 hexanes: ethyl acetate on a 24 g silica gel column. The fractions containing the desired product provided 0.59g of the title compound as a colorless oil. 1H NMR (400MHz, CHLOROFORM-d) delta 7.39 (d, J=7.3 Hz, 1H), 7.25 (t, J=7.6 Hz, 1H), 7.22 – 7.18 (m, 1H), 6.92 (d, J=8.1 Hz, 1H), 6.83 (d, J=1.7 Hz, 1H), 6.78 (dd, J=8.2, 1.8 Hz, 1H), 4.79 (d, J=5.9 Hz, 2H), 4.33 (s, 4H), 2.28 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83647-43-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHUPAK, Louis S.; ZHENG, Xiaofan; WO2015/34820; (2015); A1;,
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Synthetic Route of 3637-61-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 3637-61-4, name is Cyclopentanemethanol. A new synthetic method of this compound is introduced below.

To a suspension of Nail (98 rng, 2.5 mmol, 5 eq) in THF (5 mL) at 0C cyclopentanernethanol (263 iL, 2.5 mrnol, 5 eq) was added. The reaction was stirred at 0C for 30 mm and 6-(6-bromopyridin-2-yl)-3 -[(2-chloro-4-fluorophenyl)sulfanyl]- 6-(thiophen-3-yI)piperidine-2,4-dione (250 mg, 0.49 mmol, I eq) was added. The reaction was then stirred overnight under reflux and quenched by the addition of water (10 mL) and HCI 1M (5 mL). The aqueous phase was extracted with ethyl acetate (3 x 15 mL) and the combined organic phases were dried with Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (eluent: heptane/ ethyl acetate: 75/25) to give 3- [(2-chloro-4-fluorophenyl)sulfanyl]-6-[6-(cyclopentylmethoxy)pyridin-2-yl] -6- (thiophen-3-yl)piperidine-2,4-dione (192 mg, 0.36 mmol) in 74 % yield.?H NMR (MeOD-d4, 400 MHz): 6 7.71 (dd, .1 8.0, 7.6 Hz, 1H), 7.44 (dd, J 8.8, 7.2 Hz, I H), 7.27 (dd, .1 = 2.8, 1 .2 Hz, 1 H), 7.1 5-7.1 1 (m, 2H), 7.09 (dd, J 4.8, 2.8 Hz. 11-1), 6.75 (d,.J= 8.4 Hz, IH), 6.54 (td,.J= 8.4, 2.8 Hz, IH), 5.99 (dd,J= 8.8, 6.0 Flz, IF). 4.27-4.18 (rn, 21-1). 3.87 (d,.J= 16.4 l-lz, IH), 3.45 (d,.1 16.4 Hz, 1H), 2.36-2.28 (111, 11-1), l.83-l.74(rn, 2H), 1.66-1.53 (m, 4H), 1.39-1.29 (m, 2H).?3C NMR (MeOD-d4, 100 MHz): 6 166.9, 161.6, 158.6 (d,J 245 Hz), 157.2, 143.5, 138.2, 130.7 (d, J= 4 Hz), 124.8 (d, J 8.5 Hz), 124.7, 124.5, 120.1, 114.7 (d, J= 25 Hz), 112.3 (d, .J= 21 Hz), 111.8, 108.0, 100.0, 68.3, 59.3, 39.1, 37.3, 27.5,23.4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3637-61-4, Cyclopentanemethanol, and friends who are interested can also refer to it.

Reference:
Patent; SPERMATECH AS; GOLDING, Louise; SIENG, Bora; LUNDVALL, Steffi; B?EN, Claudia Alejandra; HNIDA, Kathrin; (68 pag.)WO2018/211276; (2018); A1;,
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