Month: March 2021

Application of 702-23-8, 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.702-23-8, name is 2-(4-Methoxyphenyl)ethanol, molecular formula is C9H12O2, molecular weight is 152.19, as common compound, the synthetic route is as follows.

To a solution of 4-methoxyphenethyl alcohol (1.03 g, 6.77 mmol) in dichloromethane (20 mL) were added N,N-diisopropylethylamine (2.3 mL, 14 mmol) and chloromethyl methyl ether (0.82 mL, 11 mmol) at 0 C. The reaction mixture was stirred for 27 h at ambient temperature. The reaction mixture was then concentrated under reduced pressure. Column chromatography (silica gel, 34 g; n-hexane/ethyl acetate, 8:1) gave the title compound (1.19 g, 6.07 mmol, 89.6%) as a pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ): delta 2.85 (t, J = 7.0 Hz, 2H), 3.30 (s, 3H), 3.72 (t, J = 7.0 Hz, 2H), 3.78 (s, 3H), 4.61 (s, 2H), 6.80-6.87 (m, 2H), 7.12-7.19 (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): delta 35.5, 55.3, 55.4, 68.8, 96.5, 113.9, 129.9, 131.1, 158.2. HR-MS (EI): Calcd for C 11 H 16 O 3 [M] + : 196.1099. Found: 196.1093. IR (neat, cm -1 ): 2936, 2836, 1613, 1514, 1247.

Statistics shows that 702-23-8 is playing an increasingly important role. we look forward to future research findings about 2-(4-Methoxyphenyl)ethanol.

Reference:
Article; Karaki, Fumika; Kuwada, Miki; Tajiri, Saki; Kanda, Misaki; Yanai, Mari; Kamimura, Mitsuhiro; Itoh, Kennosuke; Fujii, Hideaki; Synthetic Communications; vol. 49; 2; (2019); p. 212 – 220;,
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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.6642-34-8, name is (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol, molecular formula is C8H7BrO3, molecular weight is 231.04, as common compound, the synthetic route is as follows.Application In Synthesis of (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol

General procedure: To the solution of alcohol 4b (0.50 g, 2.67 mmol) and DMSO (0.41 g, 5.34 mmol) in ethyl acetate (5 ml) was added T3P (1.84 g, 6.68 mmol, 2.5 equiv, 50% solution in ethyl acetate) at 0 C. The resulting mixture was allowed to warm to RT and stirred for 1 h. Pyrazine-2-amine 3a (0.254 g, 2.67 mmol) was added to the above mixture and stirred for 15 min, which was followed by the addition of isocyanide 1c (0.33 g, 4.01 mmol) at room temperature and stirring for 4 h. Progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with ethyl acetate and neutralized with aqueous sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (25 mL ¡Á 2), the combined organic phases were washed with water, brine solution, dried over anhydrous sodium sulfate, and concentrated under vacuum to afford a crude product, which was purified on silica gel using ethyl acetate and petroleum ether.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6642-34-8, (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Ramesha, Ajjahalli B.; Raghavendra, Goravanahalli M.; Nandeesh, Kebbahalli N.; Rangappa, Kanchugarakoppal S.; Mantelingu, Kempegowda; Tetrahedron Letters; vol. 54; 1; (2013); p. 95 – 100;,
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Application of 149965-40-2, Adding some certain compound to certain chemical reactions, such as: 149965-40-2, name is (5-Bromo-2-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 149965-40-2.

5-Bromo-2-chlorophenyl)methanol (15.0 g, 67.7 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (27.5 g, 108 mmol), KOAc (19.9 g, 203 mmol), and 1,4-dioxane (100 mL) were added to a 250 mL round-bottomed flask under N2. The mixture was sparged with N2 for 5 minutes and then treated with Pd(dppf)Cl2.CH2Cl2 (4.96 g, 6.07 mmol). The mixture was sparged with N2 for another 5 minutes and then stirred at 100 C. for 16 hours before cooling to room-temperature. The resultant mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure to afford the product, which was purified by preparative HPLC (eluent: CH3CN/H2O and H2O with 0.04% NH3, 1:5 to 1:1, gradient elution) to afford pure product. The product was suspended in water (10 mL), the mixture frozen using dry ice/acetone, and then lyophilized to dryness to afford the title product (6.8 g) as a white solid. The white solid (6.8 g) was further purified by FCC (eluent:petroleum ether/ethyl acetate, 20:1 to 0:1) to afford the title compound (4.0 g, 22%). MS (ESI): mass calcd. for C13H18BClO3 268.1 m/z, found 251.0 [M-H2O+H]+. 1H NMR (400 MHz, CDCl3) delta 7.88 (s, 1H), 7.68-7.63 (m, 1H), 7.35 (d, J=7.9 Hz, 1H), 4.77 (d, J=6.4 Hz, 2H), 1.90 (t, J=6.6 Hz, 1H), 1.33 (s, 12H).

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. 149965-40-2, (5-Bromo-2-chlorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Barbay, J. Kent; Chai, Wenying; Hirst, Gavin C.; Kreutter, Kevin D.; Kummer, David A.; McClure, Kelly J.; Nishimura, Rachel T.; Shih, Amy Y.; Venable, Jennifer D.; Venkatesan, Hariharan; Wei, Jianmei; (501 pag.)US2020/55874; (2020); A1;,
Alcohol – Wikipedia,
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Synthetic Route of 1805-32-9, 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. 1805-32-9, name is 3,4-Dichlorobenzyl alcohol. A new synthetic method of this compound is introduced below.

General procedure: Ionic liquid [Dsim]HSO4 (6.5 mg, ?0.02 mmol) was added to a stirred mixture of alcohol, phenol or naphthol (1.0 mmol) and HMDS (80 mg, 0.5 mmol) at room temperature under solvent free conditions. After completion of the reaction (monitored by TLC, It should be noted that when addition of HMDS is finished stirring of the mixture is stopped after 1 min. TLC showed that in most of the cases the reaction is completed immediately after the addition of HMDS), the product was extracted with Et2O and the ionic liquid was recovered and was dried at 65 ?C under vacuum to remove moisture, and then reused. Evaporation of the solvent under reduced pressure gave the highly pure product without further purification. The desired pure products were characterized by comparison of their IR, NMR and MS data as well as boiling poin twith those of known compounds

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1805-32-9, 3,4-Dichlorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Article; Shirini, Farhad; Khaligh, Nader Ghaffari; Akbari-Dadamahaleh, Somayeh; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 15 – 23;,
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Adding a certain compound to certain chemical reactions, such as: 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

Step 1: [1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol 1,1-Bis(hydroxymethyl)cyclopropane (1.0 g, 0.0098 mol), triethylamine (TEA) (2.0 mL, 0.015 mol), and 1H-imidazole (0.13 g, 0.0020 mol) were dissolved in anhydrous DCM (15 mL) and the solution was cooled to 0 C. A solution of tert-butyldimethylsilyl chloride (1.55 g, 0.0103 mol) in DCM (5 mL) was added drop-wise and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and extracted with DCM (3*). The organic extract was dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude product was identified by 1H NMR and used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, and friends who are interested can also refer to it.

Reference:
Patent; Yao, Wenqing; Burns, David M.; Chen, Lihua; Zhuo, Jincong; He, Chunhong; US2007/197506; (2007); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 110-73-6, 2-(Ethylamino)ethanol, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

18a. Ethyl(2-(nitrooxy)ethyl)ammonium nitrate Ethyl(2-(hydroxy)ethyl)amine (5 g, 56 mmol) in EtOAc (60 mL) was added drop-wise to a mixture of fuming HNO3 (17.7 g, 11.8 mL, 280 mmol) and Ac2O (45.8 g, 42.3 mL, 448 mmol) at -10 C. The reaction mixture was stirred at -10 C. for 30 minutes and diluted with EtOAc and hexane. The oil layer was separated and dried in high vacuo to give the title compound (8.4 g, 76% yield) as a pale green oil. 1H NMR (300 MHz, d6-DMSO) delta 8.60-8.95 (bs, 2H), 4.84 (m, 2H), 3.37-3.49 (m, 2H), 3.02-3.16 (m, 2H), 1.24 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) delta 69.1, 43.6, 42.6, 11.0. Mass spectrum (API-TIS) m/z 135 (MH+).

The synthetic route of 110-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NitroMed, Inc.; US2004/24057; (2004); A1;,
Alcohol – Wikipedia,
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Synthetic Route of 7515-29-9, 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 7515-29-9, name is 1-Cyclobutylethanol. This compound has unique chemical properties. The synthetic route is as follows.

In a 20 mL reaction vial, 3-(4-bromo-phenyl)-5-methyl-3H-[l,2,3]triazole-4-carboxylic acid (300 mg, 1.06 mmol), 1-cyclobutylethanol (170 mg, 1.70 mmol) and triethylamine (218 mg, 0.3 mL, 2.15 mmol) were combined with toluene (10 mL) to give a yellow solution and to this was added diphenylphosphorylazide (585 mg, 0.458 mL, 2.13 mmol). The vial’s atmosphere was purged with nitrogen, sealed, heated in an oil bath at 65 C for 2.5 h, and cooled to room temperature overnight. The reaction was diluted with EtOAc and washed with water, saturated ammonium chloride, and brine. The aqueous layers were extracted once with EtOAc. The organic layers were combined, dried over MgS04, filtered, concentrated, diluted with DCM, and purified by flash chromatography (silica gel, 0% to 50% EtOAc in hexanes). Appropriate fractions combined, concentrated, and dried from DCM / hexanes yielding [3-(4-Bromo-phenyl)-5-methyl-3H-[l,2,3]triazol-4-yl]-carbamic acid 1-cyclopropyl-ethyl ester (295.2 mg, 73.2%> yield) as a colorless waxy solid. LC/MS calcd. for Ci6Hi9BrN402 (m/e) 378/380, obsd. 379/381 (M+H, ES+).

According to the analysis of related databases, 7515-29-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GABRIEL, Stephen Deems; HAMILTON, Matthew Michael; QIAN, Yimin; SIDDURI, Achyutharao; WO2013/189865; (2013); A1;,
Alcohol – Wikipedia,
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Related Products of 756520-66-8 , The common heterocyclic compound, 756520-66-8, name is 1-(2,6-Dichloro-3-fluorophenyl)ethanol, molecular formula is C8H7Cl2FO, 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.

Step 1: 1,3-dichloro-2-(1-bromoethyl)-4-fluorobenzene To a solution of triphenylphosphine (27.8 g, 0.106 mol) in CH2Cl2 (200 mL), liquid bromine (16.8 g, 0.105 mol) was added slowly under stirring at 0C. Upon completion of the addition, the resultant was stirred for 10 minutes, and then to which 1-(2,6-dichloro-3-fluorophenyl)ethanol (20.9 g, 0.10 mol) was added. Upon completion of the addition, the resultant was stirred for 30 minutes. The reaction was quenched with ethanol. and the reaction liquid was poured into saturated sodium bicarbonate solution, and extracted with CH2Cl2. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to give 1,3-dichloro-2-(1-bromoethyl)-4-fluorobenzene (25.8 g, 95% yield). 1H-NMR (400 MHz, CDCl3): delta = 7.28 (m, 1H), 7.05 (t, 1H), 5.97 (q, 1H), 2.16 (d, 3H).

The synthetic route of 756520-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XIAO, Dengming; XU, Xinhe; LIU, Xijie; HU, Yuandong; YU, Honghao; LIU, Zhihua; PENG, Yong; SUN, Yinghui; LUO, Hong; KONG, Fansheng; HAN, Yongxin; SUN, Jian; EP2952510; (2015); A1;,
Alcohol – Wikipedia,
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Electric Literature of 534-03-2, 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. 534-03-2, name is 2-Aminopropane-1,3-diol, molecular formula is C3H9NO2, 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.

Example 121; 3-[“2-([“3-(diethylamino)propyl]amino}-8-(2,6-difluorophenylV7-oxo-7,8- dihydropyrido[2,3-^]pyrimidin-4-yll-Lambdar-r2-hvdroxy-l-(hvdroxymethyl’)ethyl]-4- methylbenzamideTo the compound 3-[2-{[3-(diethylamino)propyl]amino}-8-(2,6- difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-(f]pyrimidin-4-yl]-4-methylbenzoic acid (40 mg, 0.074 mmol) in THF (2 mL) were added HBTU (30 mg, 0.079 mmol) and serinol (35 mg, 0.37 mmol). The mixture was stirred at rt overnight. Solvent was removed by rotovap. Separation by HPLC with TFA, followed by neutralization with SPE amine cartridge afforded the title compound (40 mg, 88%). LC-MS m/z 595 (M+H)+.

According to the analysis of related databases, 534-03-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/104915; (2006); A2;,
Alcohol – Wikipedia,
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Electric Literature of 22436-06-2, 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. 22436-06-2, name is (S)-2-Methyl-3-phenylpropan-1-ol. A new synthetic method of this compound is introduced below.

Example 115.1 g (100 mmol) of 2-methyl-3-phenylpropanol were introduced as initial charge in 87 g of dichloromethane. Over the course of 4 hours, 13.4 g (100 mmol) of AlCl3 and 9.3 g (100 mmol) of tert-butyl chloride were added at a temperature of 1-10 C. The mixture was heated to room temperature and worked-up with water and sodium hydroxide solution and the solvent was removed. This gave a mixture with the following composition: 2-methyl-3-(3-tert-butylphenyl)propanol (41%); 2-methyl-3-(4-tert-butylphenyl)propanol (24%); 3-(3,5-di-tert-butylphenyl)-2-methylpropanol (19%); 2-methyl-3-phenylpropanol (15%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22436-06-2, (S)-2-Methyl-3-phenylpropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; US2012/209030; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts