Month: June 2021

Reference of 67853-03-6, 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. 67853-03-6, name is Methyl 3-(hydroxymethyl)benzoate, 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.

To a solution of methyl 3-(hydroxymethyl)benzoate (0.30 g, 1.8 mmol) in DMF (5 mL), cooled to 0C, was added sodium hydride (60% dispersion in mineral oil, 0.086 g, 2.15 mmol). The reaction mixture was stirred at this temperature for 10 minutes and then at room temperature for 20 minutes. 2-(3-chloropropyl)-l,3-dioxalane (0.25 g, 1.8 mmol) was added and the reaction stirred room temperature for 5 hours. The reaction mixture was quenched with water and saturated aqueous sodium carbonate added. The mixture extracted with ethyl acetate (x3) and the combined organic extracts dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure. The residue was diluted with THF / MeOH (4.5 mL / 4.5 mL) and 2M aqueous sodium hydroxide (4.5 mL) added. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to half the volume and the pH adjusted with aqueous 1M hydrochloric acid. The mixture was extracted with ethyl acetate (x2) and the combined organic extracts dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford the title compound (0.25 g, 52%).

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 67853-03-6, Methyl 3-(hydroxymethyl)benzoate.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; (108 pag.)WO2017/93208; (2017); A1;,
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Application of 26021-57-8, 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.26021-57-8, name is 3,4-Dihydro-2H-benzo[b][1,4]oxazin-6-ol, molecular formula is C8H9NO2, molecular weight is 151.1626, as common compound, the synthetic route is as follows.

General procedure: To a mixture of 9 (100mg, 0.74mmol) (the general procedure for the synthesis of intermediate 9 was presented in supporting information), 3-chlorobenzaldehyde (104mg, 0.74mmol) and ethyl 2-cyanoacetate (83muL, 0.78mmol) in anhydrous EtOH (5mL) was added piperdine (136muL, 1.48mmol). The reaction mixture was stirred for 16hat 80C under N2 atmosphere. The resulting reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography eluting with CH2Cl2/MeOH (200:1-100:1, v/v) to afford the title compound (9a) as a slight yellow solid (210mg, 77% yield).

The chemical industry reduces the impact on the environment during synthesis 26021-57-8, I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Huijun; Fang, Xiong; Meng, Qian; Mao, Yujia; Xu, Yan; Fan, Tingting; An, Jing; Huang, Ziwei; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 380 – 396;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7314-44-5, name is (2,4-Dimethoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: (2,4-Dimethoxyphenyl)methanol

General procedure: In a 10 cm3 flask, 50 mg of phosphine-polyphosphazene(0.094 mmol) was dissolved in 3 cm3 anhydrous CH2Cl2 under an argon atmosphere. The resulting solution was cooled to 0 C and a solution of 0.384 mmol C2Cl6 In a 10 cm3 flask, 50 mg of phosphine-polyphosphazene(0.094 mmol) was dissolved in 3 cm3 anhydrous CH2Cl2 under an argon atmosphere. The resulting solution was cooled to 0 C and a solution of 0.384 mmol C2Cl6 in 1 cm3 anhydrous CH2Cl2 was added followed by 0.094 mmol ofthe alcohol after 5 min. After further stirring for 15 min the solvent was removed, the residue was taken up in a minimum amount of CHCl3 and the oxidized polymer was precipitated in an appropriate solvent. The polymer was removed by filtration, and washed with the precipitation solvent. The combined filtrates were evaporated to dryness and dried under high vacuum to yield the corresponding alkyl orbenzyl chlorides. in 1 cm3 anhydrous CH2Cl2 was added followed by 0.094 mmol ofthe alcohol after 5 min. After further stirring for 15 min the solvent was removed, the residue was taken up in a minimum amount of CHCl3 and the oxidized polymer was precipitated in an appropriate solvent. The polymer was removed by filtration, and washed with the precipitation solvent. The combined filtrates were evaporated to dryness and dried under high vacuum to yield the corresponding alkyl orbenzyl chlorides.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 7314-44-5, (2,4-Dimethoxyphenyl)methanol.

Reference:
Article; Koenig, Michael; Linhardt, Anne; Brueggemann, Oliver; Teasdale, Ian; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1575 – 1582;,
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Adding a certain compound to certain chemical reactions, such as: 33420-52-9, 2,2-Difluoropropan-1-ol, 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, 33420-52-9, blongs to alcohols-buliding-blocks compound. SDS of cas: 33420-52-9

To a solution of 2,2-difluoropropan-1-ol (I-10A-7b; 1.76 g, 18.3 mmol), dimethylaminopropylamine (DMAP: 157 mg, 1.3 mmol), and triethylamine (2.20 g, 3.1 ml, 22 mmol) in CH2Cl2 (15 ml) at 0 C. was added triflic anhydride (Tf2O; 6.2 g, 3.7 ml, 22 mmol). The reaction mixture initially turned a pink color, then a yellow color following the complete addition of Tf2O. The reaction mixture was stirred at 0 C. for 2 hours and diluted with CH2Cl2. The organic solution was washed with water, 1 M aqueous citric acid, and saturated aqueous NaHCO3, dried, and concentrated under reduced pressure (225 mm/Hg; bath temperature -30 C.) to give the desired product, trifluoromethanesulfonic acid 2,2-difluoropropyl ester (I-10A-7c), as a pink oil (3 g, 72%): 1H NMR (400 MHz, CDCl3) delta 4.49 (t, J=10.8 Hz, 2H), 1.74 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; Pfizer Inc.; US2004/214837; (2004); A1;,
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Reference of 10029-04-6 , The common heterocyclic compound, 10029-04-6, name is Ethyl 2-(hydroxymethyl)acrylate, molecular formula is C6H10O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a stirred solution of 2-hydroxymethyl-acrylic acid ethyl ester (260 mg, 2 mmol) and imidazole (163 mg, 2.4 mmol) in dry DMF (5 ml) was added tert- butyldimethylsily. chloride (362 mg, 2.4 mmol). The reaction mixture was stirred overnight and diluted with ether, washed with water three times and dried over MgSO4. Solvent was removed under reduced pressure to provide a crude product that was purified by column chromatography using a solution of ethyl acetate in hexanes (1 :6) to obtain the title product (463 mg, 95%).

The synthetic route of 10029-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
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Application of 495-76-1, 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. 495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol. A new synthetic method of this compound is introduced below.

To a round-bottomed flask were added piperonyl alcohol (4) (2 mmol, 304 mg) and dichloromethane (20 mL). The mixture was cooled to 0 oC under stirring and anhydrous conditions. Then, a solution of phosphorus tribromide (10 mmol, 2.71 g, 0.9 mL) in dichloromethane (9.1 mL) was added dropwise using syringe and needle. The reaction was maintained under stirring and anhydrous conditions at room temperature for 3 h. Afterwards, distilled water (50 mL) was added to the mixture, which was extracted with CH2Cl2 (3 x 50 mL). The organic phase was dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using hexane/ethyl acetate (10:1) as eluent to afford the desired product 3. Yield: 371 mg (86%); off-white solid; m.p. 40-41 oC (m.p. lit.11 39 oC); Rf = 0.44 (eluent: hexane/ethyl acetate (10:1)); 1H NMR (300 MHz, CDCl3): delta 6.85 (d, J = 8.7 Hz, 2H), 6.74 (d, J = 7.9 Hz, 2H), 5.96 (s, 2H), 4.45 (s, 2H); 13C NMR (75 MHz, CDCl3): delta 147.9, 147.8, 131.5, 122.7, 109.4, 108.3, 101.3, 34.2; IR (KBr, cm-1) 3448.7, 2900.9, 1500.6, 1485.2, 1251.8; GC/MS (m/z, %): 214 (10.0), 215 (9.9), 135 (100.0), 77 (23.8), 51 (16.3), 105 (7.0).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,495-76-1, Benzo[d][1,3]dioxol-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Article; Correa, Bianca K.; Silva, Tamiris R.C.; Raminelli, Cristiano; Tetrahedron Letters; vol. 59; 39; (2018); p. 3583 – 3585;,
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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.928-51-8, name is 4-Chlorobutan-1-ol, molecular formula is C4H9ClO, molecular weight is 108.5667, as common compound, the synthetic route is as follows.name: 4-Chlorobutan-1-ol

To a suspension of 4-ethynyl-1H-pyrazole (920 mg, 10 mmol) and4-chlorobutan- 1-ol (216 mg, 20 mmol) in acetonitrile (25 mL) was added K2C03 (4.1 g,30 mmol, 3 eq) and KI (166 mg, 1 mmol, 0.1 eq). The mixture was stirred for 6 hours at85 C under N2 protection. The readion mixture was quenched with water and extractedwith EtOAc. The residue was purified by chromatography (DCM:MeOH 10:1) to afford to afford 1.3 g of 4-(4-ethynyl-1H-pyrazol-1-yl)butan-1-ol with 80% yield. ESI-MS mlz 165.02 [M+Hjt

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928-51-8, 4-Chlorobutan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; HU, Yang; QIN, Chong; XU, Fuming; HU, Jiantao; XIANG, Weiguo; ZHOU, Bing; (233 pag.)WO2018/52949; (2018); A1;,
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Reference of 52273-77-5, 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 52273-77-5, name is 2-(3-Aminophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Step B: 2-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol Into a reaction flask were added 2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (0.33 g, 1.2 mmol) (prepared according to Example 1, step A), 1,4-dioxane (20 mL), 2-(3-aminophenyl)ethanol (0.22 g, 1.6 mmol), and p-toluenesulfonic acid monohydrate (0.080 g, 0.42 mmol). The mixture was heated at 105 C. for 3 hours and then an aqueous solution of NaHCO3 (saturated) was added. The organic solvent was removed under vacuum followed by the addition of water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, and concentrated under vacuum. The crude was purified by silica gel column chromatography to provide the desired product as a white solid (0.33 g, 74% yield). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

According to the analysis of related databases, 52273-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; US2010/190804; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 329218-12-4, 3-Bromo-4-chlorobenzyl Alcohol, 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, 329218-12-4, blongs to alcohols-buliding-blocks compound. Formula: C7H6BrClO

Example 12 4-Aminomethyl-cyclohexanecarboxylic acid {1-[3-(3-amino-1H-indazol-6-yl)-4-chloro-phenyl]-2-phenyl-ethyl}-amide 12A. 3-Bromo-4-chloro-benzaldehyde: To a cooled (0 C.), clear, colorless solution of 3-bromo-4-chlorobenzoic acid (1.0 g, 4.25 mmol) in THF (43 mL) was added dropwise a 1.0 M borane-THF complex (12.7 mL, 12.7 mmol). After 15 min, the reaction was warmed to rt and then to reflux. After 2 h, the reaction was cooled to rt, then to 0 C., and then quenched with MeOH (10 mL). The reaction was warmed to rt and after 15 min., the reaction was concentrated. The residue was dissolved in EtOAc and washed with 1.0 N HCl, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give a clear, colorless liquid. The liquid was dissolved in CH2Cl2 (17 mL) and cooled to 0 C. Next Dess-Martin periodinane (2.16 g, 5.10 mmol) was added. The resulting cloudy pale orange suspension was stirred for 30 min. and then diluted with Et2O (50 mL). The reaction was filtered through a plug of silica gel and the filtrate was concentrated to give an off-white solid. Column chromatography on silica gel (gradient elution 0-25% EtOAc in Hex) gave 0.815 g (87%) of the aldehyde as a white solid. 1H NMR (400 MHz, CDCl3) delta: 9.94 (s, 1H), 8.13 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.1, 2.0 Hz, 1H), 7.63 (d, J=7.9 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,329218-12-4, its application will become more common.

Reference:
Patent; Corte, James R.; Quan, Mimi L.; Smallheer, Joanne M.; Pinto, Donald J.; US2006/154915; (2006); A1;,
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Synthetic Route of 68327-04-8, Adding some certain compound to certain chemical reactions, such as: 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride,molecular formula is C5H12ClNO, 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 68327-04-8.

To a mixture of 4-bromo-l-hydroxy-2-naphthoic acid (5.00 g) , (IS, 2S) -2-aminocyclopentanol hydrochloride (2.71 g) , HATU (9.25 g) and DMF (30 mL) was added triethylamine (7.83 mL) at 0C, and the mixture was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with a mixed solvent of ethyl acetate and THF. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under, reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the titlecompound (1.69 g) .MS: [M-H]~347.9, 349.9

According to the analysis of related databases, 68327-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
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