Month: March 2022

Application of 5617-32-3 , The common heterocyclic compound, 5617-32-3, name is 3,6,9,12,15,18-Hexaoxaicosane-1,20-diol, molecular formula is C14H30O8, 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.

6.2 3,6,9,12,15,18,21-Heptaoxahexacos-25-en-1-ol (2) To an anhydrous THF solution of NaH (0.39 g of 45percent in mineral oil, 10.1 mmol) was added heptaethylene glycol (1, 3 g, 9.2 mmol) drop wise at 4 °C. After 30 min, 1-bromopentene (1.18 mL, 10.1 mmol) was added slowly to the above solution. The reaction mixture allowed to warm to room temperature and then stirred under N2 for 14 h. The reaction was quenched by addition of methanol at 0 °C, the solvent was evaporated and 200 mL of water was added to the residue which was then extracted with ethyl acetate (100 mL, 3*). The organic layers were washed with brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure. Purification by flash column chromatography over silica gel with 1percent methanol in dichloromethane gave pure color less oil 2: Rf: 0.41 (4percent MeOH in DCM); yield: 1.86 g, 52percent, 1H NMR (400 MHz; CDCl3) delta 5.82 (ddtd, J = 16.9, 10.2, 6.6, 1.9 Hz, 1H), 5.07-4.90 (m, 2H), 3.79-3.53 (m, 28H), 3.47 (td, J = 6.7, 1.8 Hz, 2H), 2.61 (t, J = 6.2 Hz, 1H), 2.11 (dtt, J = 8.0, 6.7, 1.4 Hz, 2H), 1.74-1.62 (m, 2H); 13C NMR (CDCl3; 100 MHz) delta 132.2, 114.6, 77.4, 76.9, 76.6, 70.6, 70.5, 70.0, 69.9, 50.6, 30.2, 28.7; MS m/z [M+H]+ calcd for C19H39O8 394.2, found 394.2; MS m/z [M+Na]+ calcd for C19H38O8Na 417.2, found 417.2.

The synthetic route of 5617-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Biswas, Souvik; Medina, Scott H.; Barchi, Joseph J.; Carbohydrate Research; vol. 405; (2015); p. 93 – 101;,
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Application of 17366-48-2 ,Some common heterocyclic compound, 17366-48-2, molecular formula is C7H14ClNO, 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.

General procedure: General Method F (copper catalyzed amination of aryl-hal) A microwave vial was charged with 1 ,4-diiodobenzene or l-bromo-4-iodobenzene (1.0 equiv), Cul (20 mol%), BINOL (20 mol%), and K3P04 (2 equiv.). The vial was capped and then evacuated and backfilled with Ar. Dialklyamine (1.2 equiv) and DMF were then added. The resulting mixture was stirred at rt for 2 to 4 d. The mixture was diluted with EtOAc, filtered through a cake of Celite and the filtrate was concentrated to give the crude product. Crude product was purified by flash chromatography to give the title compound.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 17366-48-2, exo-8-Azabicyclo[3.2.1]octan-3-ol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LIU, Yong; LANG, Yunhui; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LAUFER, Radoslaw; PATEL, Narendra Kumar B.; SAMPSON, Peter Brent; FEHER, Miklos; AWREY, Donald E.; WO2014/56083; (2014); A1;,
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Synthetic Route of 1051899-73-0, 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. 1051899-73-0, name is (3-Amino-2-fluorophenyl)methanol, molecular formula is C7H8FNO, 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.

Intermediate 102: ethyl [2-fluoro-3-(hydroxymethyl)phenyl]carbamate A stirred suspension of sodium carbonate (78 mg, 1.573 mmol) and Intermediate 101 (222 mg, 1.573 mmol) in 10 mL of water was cooled at 0 C. under nitrogen atmosphere. Ethyl chlorocarbonate (ALDRICH, 171 mg, 1.573 mmol) was added dropwise. Reaction was stirred for 1 h 30 min at 0 C. and then allowed to reach room temperature. Crude of reaction was partitioned with Et2O. Organic layers were dried with MgSO4 (anh), filtered and concentrated to obtain the title compound (359 mg, 1.600 mmol, quantitative yield). 1H NMR (300 MHz, DMSO-d6) 8 ppm: 9.21 (br s, 1H), 7.45-7.55 (m, 1H), 7.05-7.22 (m, 2H), 5.24 (br s, 1H), 4.51 (s, 2H), 4.10 (q, 2H), 1.22 (t, 3H). [ES+MS] m/z 214 (MH+).

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 1051899-73-0, (3-Amino-2-fluorophenyl)methanol.

Reference:
Patent; Ballell Pages, Lluis; Castro Pichel, Julia; Fernandez Menendez, Raquel; Fernandez Velando, Esther Pilar; Gonzalez Del Valle, Silvia; Leon Diaz, Maria Luisa; Mendoza Losana, Alfonso; Wolfendale, Matthew James; US2012/95064; (2012); A1;,
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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. 13651-14-4, name is (2,3-Dimethylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of (2,3-Dimethylphenyl)methanol

In a fixed-bed reactor having an inner diameter of 10 mm, 1 g of the Cu5wt%-Pd4wt%-K5wt%/Al203 catalyst prepared in Example 1 was charged in a constant temperature zone of the reaction tube, and both ends were filled with quartz sand and quartz wool to ensure the reaction. The airflow was stable and evenly distributed. The sealing device was reductively activated with hydrogen (25 ml/min) at 350 C for 7 hours. Then change the carrier gas to argon and the argon flow was adjusted to 200ml/h and pressure to 3.5MPa. Then the temperature was adjusted to 150C; The reaction was started by continuously feeding o-nitroaniline:fatty alcohol:distilled water according to a mass ratio of 1:12:10 with a high pressure pump. The feed flow of o-nitroaniline, fatty alcohol, and distilled water was 0.7 g/liter/h. After the reaction product was cooled by the condenser and then entered the gas-liquid separator, the liquid product was collected. The results of the experiments with different fatty alcohols are shown in Table 2.

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, 13651-14-4, (2,3-Dimethylphenyl)methanol.

Reference:
Patent; Zhejiang University of Technology; Zhang Qunfeng; Cheng Zheng; Feng Feng; Xu Xiaoliang; Ma Lei; Lu Chunshan; Li Xiaonian; (12 pag.)CN105037274; (2018); B;,
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Electric Literature of 1994-13-4, 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.1994-13-4, name is 6-Fluoro-4-hydroxy-2H-chromen-2-one, molecular formula is C9H5FO3, molecular weight is 180.1326, as common compound, the synthetic route is as follows.

Compound 31: 8-Fluoro-3-(6-fluoro-4-hydroxy-2-oxo-2H-chromene-3-yl)-2-hydroxy- 2, 3-DIHYDRO-4H-FUROF3, 2-CLCHROMENE-4-ONE; Example 31; 6-Fluoro-4-hydroxycoumarin (180 mg; 1.0 mmole) was mixed with a 40 % aqueous solution of glyoxal (574 muL ; 5.0 mmole). Acetonitrile (8 mL) was added thereto and the reaction mixture was refluxed for 6 hours. By cooling the solution to room temperature a white precipitate was precipitated, which was filtered and washed with acetonitrile. There were obtained 62 mg (31 %) of compound 31, which did not need additional purification. 1H-NMR (300 MHz, DMSO-D6) No./PPM : 4. 85 (bs, 1H); 6.35 (bs, 1H); 7.40-7. 84 (m, 6H); 9.36 (bs, 1H); 3C-NMR (75.4 MHz, DMSO-D6) D/PPM : 42.8 ; 101.0 ; 101.6 ; 107.1 (D, J = 24.8 Hz) ; 108.1 (d, J = 25.7 Hz); 108. 6; 111.9 (d); 115.9 (d); 117.4 (d); 117.8 (d); 118.7 (d, J = 23.0 Hz); 119.0 (d, J= 20 Hz); 147.4 ; 149.7 ; 156.7 (d, 241 Hz); 158. 1 (d, 236 Hz); 160.2 ; 162.2 ; 163.1 ; 165.4 ; MS m/z : ES- (acetonitrile: water) [M-H]-: 399.0.

The chemical industry reduces the impact on the environment during synthesis 1994-13-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2005/10006; (2005); A1;,
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Electric Literature of 17366-48-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17366-48-2 as follows.

1-(Diphenylmethyl)azetidin-3-one (see Bioorg. Med. Chem. Lett.; 13; 2003; 2191-2194, 2.12 g, 9.0 mmol) was dissolved in methylene chloride (25 mL) and the resultant solution was added to a slurry of exo-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (norpseudotropine hydrochloride) (see U.S. Pat. No. 6,699,870, 2.12 g, 9.0 mmol) in methylene chloride (25 mL). Another portion of methylene chloride (20 mL) was added and then DIPEA (3.47 g, 26.8 mmol), acetic acid (1.09 g, 18.2 mmol) and sodium triacetoxyborohydride (3.79 g, 17.9 mmol) were added in the given order. The mixture was stirred at RT for 4 days and then diluted with methylene chloride (150 mL). The solution was washed with a mixture of aqueous Na2CO3 (sat. 20 mL) and aqueous NaHCO3 (sat. 15 mL) and then washed with aqueous NaHCO3 (sat. 15 mL). The organic solution was dried (Na2SO4) and then the solvent was removed by evaporation. The product was purified twice by column chromatography on silica gel first eluting with methylene chloride/methanol (95/5) and then with methylene chloride/ammonia saturated methanol (9/1). There was obtained 1.9 g (60%) of exo-8-[1-(diphenylmethyl)azetidin-3-yl]-8-azabicyclo[3.2.1]octan-3-ol as a white foam. 1H NMR (400 MHz, CDCl3). 1.4-1.6 (m, 4H), 1.7-2.0 (m, 4H), 2.8-2.9 (b, 2H), 3.1 (b, 2H), 3.3-3.5 (m, 3H), 3.8-3.9 (m, 1H), 4.4-4.5 (s, 1H), 7.2 (m, 2H), 7.3 (m, 4H), 7.4 (m, 4H); LCMS: m/z 349 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17366-48-2, its application will become more common.

Reference:
Patent; Antonsson, Thomas; US2008/146538; (2008); A1;,
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Related Products of 1875-89-4 , The common heterocyclic compound, 1875-89-4, name is 2-(m-Tolyl)ethanol, molecular formula is C9H12O, 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.

Example 306: 2-[1-(4-Chlorophenylsulfonyl)-3-(3-methylphenyl)propyl]-1,4-difluorobenzene In a similar manner to Example 304 except for the use of 2-(3-methylphenyl)ethanol (90.0 mul, 0.661 mmol), the title compound (115 mg, 0.273 mmol, 83percent) was obtained as colorless plate crystals.1H-NMR (400 MHz, CDCl3) delta: 2.29(3H,s), 2.35-2.48(2H,m), 2.56-2.64(1H,m), 2.68-2.77(1H,m), 4.46-4.49(1H,m), 6.83-6.88(3H,m), 6.97-7.03(2H,m), 7.14(1H,t,J=7.8Hz), 7.26(1H,ddd,J=8.7,5.4,3.3Hz), 7.36(2H,d,J=8.6Hz), 7.49(2H,d,J=8.6Hz). IR (ATR) cm-1: 3072, 2969, 1581, 1496, 1475, 1423, 1394, 1319, 1276, 1211, 1147, 1081, 1012. mp: 87-88°C. MS m/z: 421 (M++H).Anal. calcd for C22H19ClF2O2S: C, 62.78; H, 4.55; Cl, 8.42; F, 9.03; S, 7.62. Found: C, 62.58; H, 4.60; Cl, 8.49; F, 9.21; S, 7.77.

The synthetic route of 1875-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
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Related Products of 13588-28-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 13588-28-8 as follows.

EXAMPLE 1 16 Parts of 1,4-dihydroxynaphthalene was added to 100 parts of dipropylene glycol monomethyl ether in a reaction vessel provided with a stirrer under a nitrogen atmosphere at room temperature. 42.5 Parts of 28% sodium methylate was added dropwise thereto. Then the reaction mixture was heated to 180 C. and maintained at this temperature for 1 hour. During this period, 36 parts of a distillate mainly composed of methanol was removed out of the reaction system. After cooling to 110 C., carbon dioxide gas was blown into the reaction mixture under atmospheric pressure. Although the absorption of the carbon dioxide gas was completed within 15 minutes, carbon dioxide gas was further blown for additional 15 minutes. 1,4-Dihydroxy-2-naphthoic acid produced in the reaction mixture was isolated in the following manner:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13588-28-8, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; Sumika Fine Chemicals Co., Ltd.; US5599971; (1997); A;,
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Electric Literature of 13588-28-8, 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. 13588-28-8, name is 2-(2-Methoxypropoxy)propan-1-ol. A new synthetic method of this compound is introduced below.

In a 500 mL flask, feed NaOH tablets 55. 2 g (relative to the following DPMI moles,Equivalent to 1. 5 moles)And 1-bromo-3-methylbutane(Manufactured by Yancheng Longsheng Chemical Co., Ltd.) (hereinafter also referred to as “IABr”) 163.5 g (relative to the following DPMI moles,Equivalent to 1. 2 moles)Start stirring.After raising the liquid temperature to 45 C,While keeping the temperature inside the system at 45 C,DPM133. 7 g was added dropwise over 6 hours.Thereafter,Stirring was carried out while maintaining a 45 C condition.In addition,The low boiling compounds produced in the above reaction were measured using a gas flow meter and gas chromatography3-methyl-1-butene.To the reaction solution was added water 155. 7 g was subjected to extraction / separation,The results of the analysis of the obtained organic phase 222. 5 g using gas chromatography,Got 125. 0gOf dipropylene glycol methyl isopentyl ether(Isomer mixture) (hereinafter also referred to as “”DPMIA”).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13588-28-8, 2-(2-Methoxypropoxy)propan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Daicel Corporation; Mori, Atsushi; (9 pag.)CN105503545; (2016); A;,
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Application of 155310-11-5, 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. 155310-11-5, name is 3-Amino-2,2-difluoropropan-1-ol, molecular formula is C3H7F2NO, 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.

General procedure: To a solution of 4-chloro-1-fluoro-2-nitro-benzene (2.6 mmol)and amine (2.6 mmol), K2CO3 (5.2 mmol) in DMF (10 mL) wasadded TEA (5.2 mmol). The mixture was then stirred at 100 C for2 h. After the reaction was complete, the mixture was poured intowater (30 mL) and extracted with EtOAc (30 mL) three times. Thecombined organic layer was washed with brine (20 mL), dried overNa2SO4 and then concentrated in vacuo. The residue was thenpurified by column chromatography on silica gel to give 4-chloro-N(R2)-2-nitro-aniline. To a solution of 4-chloro-N(R2)-2-nitro-aniline (2.2 mmol) andhydrazine hydrate (1 mL) in the mixed solvent of MeOH (5 mL) andTHF (5 mL) was added Raney Ni (5%e10% loading). The mixturewasthen stirred at room temperature for 1-2 h. LC-MS showed completeconversion of start material. The mixture was then filteredand the filtrate was concentrated in vacuo to give the crude of 4-chloro-N1(R2)-benzene-1,2-diamine, which was used in the nextstep without further purification. A mixture of 4-chloro-N1(R2)-benzene-1,2-diamine (1 mmol)and sodium chloroacetate (130 mg, 1.1 mmol) in 4N HCl was heatedto 100 C overnight. After the reaction was complete, the mixturewas concentrated in vacuo to remove the solvent and the residuewas dissolved in DCM (100 mL). The solutionwas thenwashed withsat NaHCO3 (50 mL), brine, dried over MgSO4 and concentrated invacuo. The residue was purified by column chromatography onsilica gel (DCM/EA 3/1) to give 5-chloro-2-(chloromethyl)-1-R2-benzimidazole.To a mixture of 3-methylsulfonyl-1H-pyrazolo[3,4-c]pyridine(0.89 mmol) and 5-chloro-2-(chloromethyl)-1-R2-benzimidazole(0.74 mmol) in DMF (5 mL) was added K2CO3 (204 mg,1.48 mmol) and the mixture was stirred at rt overnight. After thereaction was completed, the mixture was filtered and the filtratewas purified by preparative HPLC to give final product. To a mixture of 3-methylsulfonyl-1H-pyrazolo[3,4-c]pyridine(0.89 mmol) and 5-chloro-2-(chloromethyl)-1-R2-benzimidazole(0.74 mmol) in DMF (5 mL) was added K2CO3 (204 mg,1.48 mmol) and the mixture was stirred at rt overnight. After thereaction was completed, the mixture was filtered and the filtratewas purified by preparative HPLC to give final product.

According to the analysis of related databases, 155310-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Song; Li, Chao; Chen, Dongdong; Zheng, Xiufang; Yun, Hongying; Gao, Lu; Shen, Hong C.; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 1147 – 1157;,
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