Month: March 2021

Electric Literature of 162744-59-4 ,Some common heterocyclic compound, 162744-59-4, molecular formula is C7H5BrF2O, 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.

A solution of methanesulfonyl chloride (4.72 ml; 60.794 mmol) in anhydrous dichloromethane (10 ml) was added dropwise (over 5 min.) to an ice-cooled solution of 4-bromo-2,6-difluorobenzyl alcohol (11.300 g; 50.669 mmol) and triethylamine (14.1 ml; 101.338 mmol) in dichloromethane (200 ml). The resulting solution was stirred at 0C, under nitrogen, for 30 min. The reaction mixture was diluted with ethyl acetate (200 ml), and water (100 ml) was added. The organic layer was successively washed with 1 N aqueous hydrochloric acid (100 ml), saturated aqueous NaHCU3 (100 ml), and finally with brine (100 ml). The organic layer was then dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to give an orange solid which was additionally dried under HV (15.170 g; 99.5%). LC-MS for the mesylate: tR = 0.92 min.; [M+H]+: no ionisation.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,162744-59-4, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/26149; (2008); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 456-47-3, 3-Fluorobenzyl 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, COA of Formula: C7H7FO, blongs to alcohols-buliding-blocks compound. COA of Formula: C7H7FO

Aniline (46.5 mg, 0.5 mmol),Cat.[Ir] (5.4 mg, 0.005 mmol, 1 mol%), cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.),3-Fluorobenzyl alcohol (75.6 mg, 0.6 mmol) and t-amyl alcohol (1 ml) were sequentially added to a 5 mL round-bottomed flask.The reaction mixture was refluxed in air for 12 hours and then cooled to room temperature.The solvent is removed by rotary evaporation and then passed through column chromatography (developer:Petroleum ether/ethyl acetate gives the pure target compound, yield: 95%.

The synthetic route of 456-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Fan Hongjun; Li Shun; Liu Pengcheng; Li Feng; (9 pag.)CN107778182; (2018); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 769-30-2, name is Benzo[d][1,3]dioxol-4-ylmethanol, molecular formula is C8H8O3, 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. Formula: C8H8O3

Benzo[d][1,3]dioxo-4-ylmethanol (223 mg, 1.47 mmol)Dissolved in dichloromethane (10 mL), then phosphorus tribromide (0.17 mL, 1.8 mmol) was added dropwise at 0 C.After the completion of the dropwise addition, the mixture was stirred at room temperature for 3 hours.The reaction was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (50 Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ¡¤geerdeman; (79 pag.)CN108690016; (2018); A;,
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Electric Literature of 1875-88-3, 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. 1875-88-3, name is 2-(4-Chlorophenyl)ethanol, molecular formula is C8H9ClO, 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.

In a 1 L pressure vessel, 4-chlorophenylethanol (412.8 g, 2636 mmol) was stirred and heated to an internal temperature of -91 0C. The system was held under reduced pressure (~ – 0.98 bar) for ~2 min. Hydrogen bromide gas was gradually charged into the pressure vessel and the reaction was stirred at an internal pressure between +0.69 and +1.65 bar for 135 min. The vessel was allowed to slowly vent to a caustic scrubber and flushed with nitrogen gas for ~ 5 min. Conversion to the bromide was found to be 4.27% by HPLC. The reaction mixture was allowed to cool to ambient temperature overnight under nitrogen. The mixture was then heated once more in an oil bath set at 96 0C and the vessel was evacuated. The vessel was gradually filled with hydrogen bromide gas and stirred at an internal pressure between +1.38 and +1.65 bar for 2 h. Conversion to the bromide was found to be 92.67 % by HPLC. The reaction was held at a bath temperature of 96 0C at atmospheric pressure for 45 min. The vessel was then evacuated and slowly backfilled with hydrogen bromide gas over 15 min to +1.38 bar. After stirring for a further 2.5 h at +1.24 to +1.38 bar, the vessel was vented to the caustic scrubber and held at a bath temperature of 96 0C in closed system at atmospheric pressure. Conversion to the bromide was found to be 99.49% by HPLC with a peak area purity of 98.71%.In order to test stability and impurity formation, the pressure vessel was then evacuated and gradually back filled with hydrogen bromide gas to an internal pressure of +1.03 bar. The dark brown suspension was allowed to stir at +1.03 bar at a bath temperature of 96 0C. After 15 h the internal pressure had risen to +2.41 bar and the vessel was vented to the caustic scrubber, purged with nitrogen, and allowed to cool to ambient temperature. The peak area purity was found to be 96.06%. The reaction mixture was transferred to a seperatory funnel and allowed to separate at room temp. The upper product phase was washed with water (412 mL) in 2 portions to leave a milky beige suspension (563.4 g) with an HPLC peak area purity of 99.29%.

According to the analysis of related databases, 1875-88-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/111004; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 16545-68-9, Cyclopropanol, 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, name: Cyclopropanol, blongs to alcohols-buliding-blocks compound. name: Cyclopropanol

Diisopropylethylamine (0.142 mL, 0.811 mmol), HBTU (0.184 g, 0.486 mmol), and crude cyclopropanol (0.0470 g, 0.811 mmol) were added to a solution of 2-(2-(3-(4-(dimethylamino)piperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetic acid (0.100 g, 0.324 mmol) in chloroform (6.0 mL) at room temperature, and the reaction liquid was stirred at the same temperature for 16 hours. Hydrochloric acid (1.0 N) was added to the reaction liquid, and then the reaction liquid was back-extracted. A saturated aqueous solution of sodium hydrogencarbonate was added to the obtained aqueous layer for neutralization, and then the resulting mixture was extracted with chloroform. The organic layer was washed with a 10% aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to obtain cyclopropyl 2-(2-(3-(4-(dimethylamino)piperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate (0.0610 g, 0.175 mmol, 54%) (hereinafter referred to as a ?compound of Example 44?) as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16545-68-9, Cyclopropanol, and friends who are interested can also refer to it.

Reference:
Patent; TORAY INDUSTRIES, INC.; MORITA, YASUHI; IZUMIMOTO, NAOKI; ISEKI, KATSUHIKO; IWANO, SHUNSUKE; UDAGAWA, SHUJI; MIYOSHI, TOMOYA; OSADA, YUJI; KOREEDA, TETSURO; MURAKAMI, MASANORI; SHIRAKI, MOTOHIRO; TAKAHASHI, KEI; OSHIDA, KEIYU; (177 pag.)TW2016/2093; (2016); A;,
Alcohol – Wikipedia,
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Reference of 5020-41-7, 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.5020-41-7, name is 2-(3-Methoxyphenyl)ethanol, molecular formula is C9H12O2, molecular weight is 152.1904, as common compound, the synthetic route is as follows.

28.90 g (0.217 mol) of aluminum chloride was slurried in 400 mL of methylene chloride under a N2 atmosphere and cooled to 0 C. 15.0 g (0.0985 mol) of 2-(3-Methoxy-phenyl)-ethanol and 17.02 g (0.217 mol) of acetyl chloride were combined in methylene chloride and following the exotherm, this solution was added dropwise to the aluminum chloride slurry at 0 C. The reaction mixture was allowed to stir at 0 C. for 1 h and at ambient temperature for 45 min. The reaction was carefully poured into 1M HCl (300 ml) and the aqueous layer was extracted with dichloromethane (3×100 ml) and the combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford crude product which was loaded onto a silica gel column. Using 20% ethyl acetate in hexane yielded 17.94 g (77%) of Acetic acid 2-(2-acetyl-5-methoxy-phenyl)-ethyl ester 38. 1H NMR (CDCl3): 2.00 (s-3H), 2.54 (s-3H), 3.24 (t-2H), 3.84 (s-3H), 4.28 (t-2H), 6.75-6.81 (m-2H), 7.77 (d-1H; J=8.52 Hz).

Statistics shows that 5020-41-7 is playing an increasingly important role. we look forward to future research findings about 2-(3-Methoxyphenyl)ethanol.

Reference:
Patent; Pfizer Inc., Pfizer Inc.; US2004/77853; (2004); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 75853-18-8, 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. 75853-18-8, name is 2,3-Difluorobenzyl alcohol. A new synthetic method of this compound is introduced below.

Example 218: 4-[2-(2,3-Difluorobenzyloxy)ethyl]piperidine-l-carboxylic acid tert-butyl esterA stirred solution of (2,3-difluorophenyl)methanol (50 mg, 350 mumol) in anhydrous THF (2 mL) was treated with tBuOK (47 mg, 42 mumol) and then 4-(2-methanesulfonyloxy- ethyl)piperidine-l-carboxylic acid tert-butyl ester (Preparation 10) was added. The resulting mixture was heated under reflux for 12 h, cooled and poured into saturated aqueous NH4Cl, and extracted with EtOAc (20 mL). The organic phase was washed with brine (5 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography (IH-EtOAc, 4: 1) to afford the title compound: RT = 4.39 min; m/z (ES+) = 356.1 [M+ H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75853-18-8, 2,3-Difluorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; PROSIDION LIMITED; WO2007/3962; (2007); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 111-90-0, 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 111-90-0, name is Diethylene Glycol Monoethyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

59-1) Synthesis of 2-(2-ethoxyethoxy)ethyl 4-methylbenzenesulfonate 432 mg (3.22 mmol) of 2-(2-ethoxyethoxy)ethanol was dissolved in 40 ml of dichloromethane, and 0.6 ml (4.19 mmol) of triethylamine and 614 mg (3.22 mmol) of p-toluenesulfonyl chloride were added thereto. The mixture was stirred at room temperature for 15 hours. After the solvent was removed under reduced pressure, 40 ml of water was added thereto. The mixture was extracted with 30 ml of ethyl acetate. The solvent was removed under reduced pressure to give 760 mg (2.64 mmol) of the title compound in a yield of 82%. 1H NMR (CDCl3, ppm): delta 1.20(3H, t), 2.35(3H, s), 3.35(2H, q), 3.52(2H, t), 3.57-3.60(4H, m), 4.08(2H, t), 7.33(2H, d), 7.78(2H, d) FAB MS(m/e)=289 [M+1]

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 111-90-0, Diethylene Glycol Monoethyl Ether.

Reference:
Patent; Lee, Jin-Ho; Hong, Chang-Yong; Park, Tae-Sik; Kim, Jong-Hyun; Choi, Sei-Hyun; Yoon, Sook-Kyung; Chung, Hyun-Ho; Jeong, Shin-Wu; Hwang, Kwang-Yeon; Shin, Dong-Kyu; US2003/149034; (2003); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 627-30-5 ,Some common heterocyclic compound, 627-30-5, molecular formula is C3H7ClO, 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 10 2-(3-Chloropropoxy)tetrahydropyran To a solution of 3-chloropropanol (20.00 g, 0.212 mol) in dichloromethane (100 mL) 3,4-dihydro-2H-pyran (16.02 g, 0.190 mol) diluted in dichloromethane (17 mL) is added dropwise at 0-5C. The mixture is stirred for 30 minutes and the reaction (checked by TLC analysis) is quenched by washing with saturated sodium bicarbonate (100 mL). After separation the organic layer is washed with water (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure at 30C (34.32 g). The title compound is isolated by column chromatography on silica gel eluding with n-hexane:ethyl acetate) (31.28 g, 0.175 mol, 91%). 1H-NMR {300 MHz, CDCl3, delta (ppm)}: 1.2-2.0 (6H); 2.09 (m, 2H, CH2); 3.56 (m, 2H, Cl-CH2); 3.70 (m, 2H, O-CH2); 3.92 (m, 2H, O-CH2); 4.65 (m, 1 H, O-CH-O). GC-MS (El): [M-H]+ = 177; [M-ClCH2CH2CH2O]+ = 85

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,627-30-5, its application will become more common.

Reference:
Patent; Newchem S.p.A.; EP2019114; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate, the common compound, a new synthetic route is introduced below. SDS of cas: 13674-16-3

EXAMPLE 116 (R)-2-[4-(6-Cyano-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid Prepared from 11-(4-hydroxy-phenyl)-benzo [b]naphtho[2,3-d]thiophene-6-carbonitrile (Example 44) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp 145-148 C.: [a]D25=-2.03 (7.883 mg/mL CHCl3); NMR (CDCl3); delta8.31 (ddd, J=8, 1, 1 Hz, 1 H), 7.78 (ddd., J=8, 1, 1 Hz, 1 H), 7.70 (ddd, J=8, 8, 1 Hz, 1 H), 7.56 (ddd, J=8, 1, 1 Hz, 1 H), 7.47-7.37 (m, 6 H), 7.32 (ddd, J=8, 7, 1 Hz, 1 H), 7.20 (dd., J=8, 2 Hz, 1 H),7.14-7.05 (m, 4 H), 6.62 (ddd, J=8, 1, 1 Hz, 1 H), 5.06 (dd, J=7, 5 Hz, 1 H), 3.44 (d, J=5 Hz, 1 H), 3.42 (d, J=7 Hz, 1 H); MS (EI): [M+], 499 (100%); Anal. Calc. for C32H21NO3S: C, 76.93, H, 4.24, N, 2.80. Found: C, 75.77, H, 4.22, N, 2.70.

The synthetic route of 13674-16-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US6110962; (2000); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts