Category: alcohols-buliding-blocks

Electric Literature of 534-03-2, 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.534-03-2, name is 2-Aminopropane-1,3-diol, molecular formula is C3H9NO2, molecular weight is 91.1091, as common compound, the synthetic route is as follows.

To a solution of 2-amino-1,3-propanediol (S2, 299 mg, 3.28 mmol, 1.0 equiv) in MeCN (10 mL), K2CO3 (2.27 g, 16.4 mmol, 5.0 equiv) and benzyl bromide (0.98 mL, 1.4 g, 8.3 mmol, 2.5 equiv) were added at room temperature. The reaction mixture was stirred at this temperature for 18 h and then diluted with water (10 mL). The aqueous layer was extracted with EtOAc (3 × 10 mL) and the combined organics were dried over Na2SO4. The solvent was removed under reduced pressure and the resultant residue was purified by column chromatography (SiO2, petroleum ether/EtOAc 1:1) to yield 716 mg (2.64 mmol, 80%) of S3 as a white solid. TLC Rf 0.20 (petroleum ether/EtOAc 1:1); mp 113 C; 1H NMR (300 MHz, C6D6): 2.30 (bs, 2H, OH), 2.93 (tt, 1H, J = 7.5, 5.9 Hz, 2-H), 3.37 (dd, 2H, J = 10.8, 5.9 Hz, 1-Ha, 3-Ha), 3.48 (dd, 2H, J = 10.8, 7.5 Hz, 1-Hb, 3-Hb), 3.53-3.66 (m, 4H, CH2Ph), 7.01-7.32 (m, 10H, Ph-H); 13C NMR (76 MHz, C6D6): 54.4, 60.2, 60.3, 127.4, 128.7, 129.2, 140.1; IR (ATR) nu 3245, 1493, 1451, 1049, 1025, 999, 741, 730, 695; UV (MeCN) lambdamax (log epsilon) 206 (4.28), 259 (2.77); MS (ESI+) m/z 272.2 (M+H+), 294.2 (M+Na+); HRMS (ESI+) m/z calcd for C17H21NNaO2 294.1465 (M+Na+), found 294.1466.

The chemical industry reduces the impact on the environment during synthesis 534-03-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Ries, Oliver; Bueschleb, Martin; Granitzka, Markus; Stalke, Dietmar; Ducho, Christian; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1135 – 1142;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 346-06-5, 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.346-06-5, name is (2-(Trifluoromethyl)phenyl)methanol, molecular formula is C8H7F3O, molecular weight is 176.14, as common compound, the synthetic route is as follows.

General procedure: To a 100 mL two-necked flask was added substituted benzylalcohol or 4,6-dimethylpyrimidine-2-thiol (2.60 mmol), NaOH (6.40 g, 1.60 mmol) and dimethylsulfoxide (30 mL). The flask was vacuumed and flushed three times with nitrogen. Then the solutionof 8 (0.20 g, 0.87 mmol) in dimethylsulfoxide (510 mL) was added, and the resulting mixture was heated to 80 C and kept at that temperature for approximately 12 h until the completion of the reaction (monitored by TLC). Subsequently, the mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The mixture was washed with brine to pH 7, and the organic phase was dried with anhydrous sodium sulfate. The organic phase was concentrated to get crude product, which was purified by column chromatography (ethyl acetate/ petroleumether 1:30 as eluent) to get 4a?ac in yields of 27.3?75.1percent.#10;#10;

Statistics shows that 346-06-5 is playing an increasingly important role. we look forward to future research findings about (2-(Trifluoromethyl)phenyl)methanol.

Reference:
Article; Lu, Huan-Huan; Xue, Ping; Zhu, Yuan-Yuan; Ju, Xiu-Lian; Zheng, Xiao-Jiao; Zhang, Xun; Xiao, Ting; Pannecouque, Christophe; Li, Ting-Ting; Gu, Shuang-Xi; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2491 – 2497;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 10160-28-8 ,Some common heterocyclic compound, 10160-28-8, molecular formula is C9H16O, 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 mixture of non-8-yn-1-ol (5.00 g, 35.6 mmol, CAS10160-28-8) and TEA (10.8 g, 106 mmol, 14.8 mL) in DCM (100 mL) was added MsCl (6.13 g, 53.4 mmol, 4.14 mL). The reaction mixture was stirred at 25 C. for 2 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was diluted with water (10 mL) and extracted with DCM (3×10 mL). The combined organic layers was dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (7.70 g, 98% yield) as light yellow oil. 1H NMR (400 MHz, CDCl3) delta 4.23 (t, J=6.4 Hz, 2H), 3.01 (s, 3H), 2.22-2.18 (m, 2H), 1.95 (t, J=2.4 Hz, 1H), 1.80-1.73 (m, 2H), 1.58-1.50 (m, 2H), 1.47-1.36 (m, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10160-28-8, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 60666-70-8, Adding some certain compound to certain chemical reactions, such as: 60666-70-8, name is (2-Bromo-5-chlorophenyl)methanol,molecular formula is C7H6BrClO, 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 60666-70-8.

Add compound 3 (500 mg, 2.26 mmol) in DCM (40 mL) and DIPEA (1.12 mL, 6.77 mmol)DMAP (55.16 mg, 451.51 mumol) was added. Then, pivaloyl chloride (416.65 uL, 3.39 mmol) was added dropwise at 0 ° C to react.The mixture was stirred at 10 ° C for 0.1 hour and then at room temperature overnight. The reaction mixture was diluted with DCM and then usedWater, 10percent citric acid and brine were washed with MgSO4 and filtered. The filtrate was concentrated to give a crude product which was purified by CC.The compound 4 (605 mg, 87.69percent) was obtained as a pale yellow oil.

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. 60666-70-8, (2-Bromo-5-chlorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Sciences Tianjin Industry Bio-technology Institute; Lin Jianping; Liu Pi; Li Jinlong; Wang Zhonghua; Liu Cui; (15 pag.)CN108264467; (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. 873-76-7, name is (4-Chlorophenyl)methanol, molecular formula is C7H7ClO, 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. category: alcohols-buliding-blocks

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mol, 5 mol%), DABCO (0.10 mol, 10 mol%), 4-HO-TEMPO (0.05 mmol, 5 mol%) were added. Substrates 1 (1 mmol) and NH3 (aq, 25-28%, 3 mmol, 3.0 equiv) in CH3CN (2 mL) were added subsequently. Then the reaction mixture was stirred at room temperature for 24 h in the presence of an air balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the corresponding products

With the rapid development of chemical substances, we look forward to future research findings about 873-76-7.

Reference:
Article; Hu, Yongke; Chen, Lei; Li, Bindong; Chinese Chemical Letters; vol. 29; 3; (2018); p. 464 – 466;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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.111-90-0, name is Diethylene Glycol Monoethyl Ether, molecular formula is C6H14O3, molecular weight is 134.1736, as common compound, the synthetic route is as follows.name: Diethylene Glycol Monoethyl Ether

Example Al 4; a. Preparation of intermediate 38; NaH (60 % in oil; 0.0072 mol) was added portionwise at 0 C to a solution of 2-(2- ethoxyethoxy)-ethanol (0.0072 mol) in THF (12.5 ml) under N2 flow. The mixture was stirred at 0C for 1 hour. A solution of intermediate 10 (0.006 mol) in THF (12.5 ml) was added dropwise. The mixture was stirred and refluxed for 18 hours and was then cooled to room temperature. EtOAc and H2O were added. The organic layer was washed with H2O and then with saturated NaCl. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. Yield: 2.5 g intermediate 38 (97 %). EPO

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111-90-0, Diethylene Glycol Monoethyl Ether, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/436; (2007); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 495-76-1, 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 495-76-1 as follows.

5-(Bromomethyl)-1,3-benzodioxole was prepared using reportedmethod [30]. Take a 250 ml round bottom flask A charged with 1,3-benzodioxole-5-methanol (5 g; 32.86 mmol) in dry diethyl ether(50 ml). Take another 100 ml round bottom flask B loaded with 3.1 ml(32.86 mmol; 1 equiv.) of phosphorous tribromide dissolved in 40 mlof diethyl ether. A dropwise addition was carried out from flask B toflask A maintaining the temperature at 0 C for and stirred for 15 min.After the completion of the reaction, the reaction mixture was workedupwithwater (3× 100ml) using a separating funnel followed bywashingwith brine (1:1). After drying over sodium sulphate and filtration,the solvent was evaporated on a vacuum rotary evaporator. The crudewas recrystallized in petroleum ether to get the desired white solidproduct.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,495-76-1, its application will become more common.

Reference:
Article; Sehrawat, Hitesh; Kumar, Neeraj; Tomar, Ravi; Kumar, Loveneesh; Tomar, Vartika; Madan, Jitender; Dass, Sujata K.; Chandra, Ramesh; Journal of Molecular Liquids; vol. 302; (2020);,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 101597-25-5, 1,1-Bis(4-methoxyphenyl)prop-2-yn-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, name: 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, blongs to alcohols-buliding-blocks compound. name: 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol

General procedure: To a refluxing solution of 5-hydroxy-3-methoxy-7H-benzo[c]fluoren-7-one 12-4 (3.00 g, 10.9 mmol) in a mixture of toluene (123 mL) and 2-butanone (45 mL) were added 1,1-bis(4-methoxyphenyl)propyn-1-ol (5.23 g, 19.5 mmol) and catalytic amount of p-TsOH, and the resulting mixture was refluxed for 30 min. The solution was cooled down to room temperature, then 10% aq. sodium hydroxide (21 mL), tetrahydrofuran (120 mL) and10% aq. sodium chloride were added and the mixture was stirred well. The organic layer was separated, washed with water four times, and the solvent removed in vacuo. To the resulting residue was added acetone (100 mL) and the mixture was refluxed for 1 h. After the mixture was cooled down, the solid material precipitated was collected by filtration. After drying in vacuo, 6-methoxy-3,3-bis(4-methoxyphenyl)benzo[3,4]fluoreno[2,1-b]pyran-13(3H)-one 13-7 was obtained as a dark purple solid (2.47 g, 4.70 mmol) in 43% yield. 13-7: Mp 207-209 C. 1H NMR (CDCl3) delta/ppm 3.77 (3H, s), 3.96 (3H, s), 6.27 (1H, d, J = 10.0 Hz), 6.84 (4H, m), 7.20 (2H, m), 7.40 (5H, m), 7.57 (2H, m), 7.80 (1H, d, J = 8.0 Hz), 7.86 (1H, d, J = 10.0 Hz), 8.27 (1H, d, J = 9.2 Hz). LC-MS 527.2033 (M+1) (Calculated exact mass for C35H27O5 (M+1) 527.1853). FT-IR (KBr) nu/cm-1 3014, 2953, 2831, 1695, 1605, 1505, 1466, 1397, 1373, 1277, 1218.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101597-25-5, 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Momoda, Junji; Izumi, Shinobu; Yokoyama, Yasushi; Dyes and Pigments; vol. 119; (2015); p. 95 – 107;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 13674-16-3 , The common heterocyclic compound, 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate, molecular formula is C10H12O3, 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.

The compound 5-hydroxy-6-nitro-1H-indazole-1-carboxylic acid tert-butyl ester (900 mg, 3.22 mmol), methyl 2-hydroxy-3-phenylpropionate (870 mg, 4.83 mmol) and triphenylphosphine (1.69g, 6.44mmol) was dissolved in dry THF (80mL) was added DIAD (1.3g, 6.44mmol) at 0 C, Stirrer at room temperature until the starting material is completely reacted.The solvent was spin dried, ethyl acetate (200mL * 3). The combined organic phases were dried, filtered, concentrated to give pale yellow solid product 5-((1-methoxy-1-carbonyl-3-phenylpropan-2-yl)oxo)-6-nitro-1H-indazole-1-carboxylic acid tert-butyl ester (1.4 g, yield 98%)

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

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Liu Shiqiang; Zhou Yuanfeng; Bao Meng; Yuan Yida; Liu Lei; Bao Rudi; (57 pag.)CN109761986; (2019); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts