Category: alcohols-buliding-blocks

Electric Literature of 2854-16-2 ,Some common heterocyclic compound, 2854-16-2, molecular formula is C4H11NO, 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 444-(cyclopropylmethoxy)-N-(2-{[(2-hydroxy-2-methylpropyl)amino]methyl}-4-methyl-1H-indol-5-yl)benzamide4-(Cyclopropylmethoxy)-N-(2-formyl-4-methyl-1H-indol-5-yl)benzamide (298 mg) obtained in Reference Example 41 and 1-amino-2-methylpropan-2-ol (153 mg) were suspended in NMP (3.0 mL), acetic acid (1.0 mL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hr.Sodium triacetoxyborohydride (363 mg) was added, the mixture was stirred at room temperature for 16 hr, and diluted with ethyl acetate, and 2N aqueous sodium hydroxide solution (20 mL) was added at room temperature.The mixture was poured into water, and the organic layer was washed with water and then with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure.The residue was suspended in ethyl acetate, and the precipitate was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (307 mg, yield 85percent) as a brown solid.1H NMR (300 MHz, CDCl3) delta: 0. 34 – 0.43 (2 H, m), 0.63-0.72 (2 H, m), 1.22 (6 H, s), 1.25 – 1.36 (1 H, m), 2.45 (3 H, s), 2.61 (2 H, s), 3.88 (2 H, d, J=7.2 Hz), 4.02 (2 H, s), 6.38 (1 H, d, J=1.1 Hz), 6.98 (2 H, d, J=8.3 Hz), 7.19 (1 H, d, J=8.3 Hz), 7.34 (1 H, d, J=7.6 Hz), 7.58 (1 H, br. s.), 7.88 (2 H, d, J=8.0 Hz), 8.48 (1 H, br. s.).melting point: 186¡ãCelemental analysis (C25H31N3O3*0.2H2O)Calculated: C, 70.63; H, 7.44; N, 9.88.Found: C, 70.57; H, 7.38; N, 9.68.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2854-16-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2522657; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 3068-00-6, 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.3068-00-6, name is 1,2,4-Butanetriol, molecular formula is C4H10O3, molecular weight is 106.1204, as common compound, the synthetic route is as follows.

General procedure: Xantphos (28.9 mg, 0.05 mmol), Cs2CO3 (32.6 mg, 0.10 mmol) and [Ru(p-cymene)Cl2]2 (15.3 mg, 0.025 mmol) were added to a Schlenk tube. Then the tube was evacuated and refilled with nitrogen. Dry toluene as solvent (2.0 mL)were added and the solution was stirred at room temperature under nitrogen for 30 min. Activated molecular sieves 4A (0.10 g) and triol 6a (106.1 mg, 1.00 mmol) were then added. And the solution was stirred at room temperature under nitrogen for 40 min. Subsequently, aniline 5a (46.6 mg, 0.50 mmol) was added and the solution was stirred at room temperature under nitrogen for 20 min. Then the resulting solution was heated to reflux and stirred for 48 h. The reaction was monitored by TLC. After completion, the solution was filtered through a plug of Celite and washed with EtOAc (3 mL x 3). The filtrate was concentrated under vacuum. Purification via flash column chromatography with silica gel (eluting with PE/EA = 5/1 (v/v)) yielded 4a (43.0 mg, 81% yield) as light yellow oil.

Statistics shows that 3068-00-6 is playing an increasingly important role. we look forward to future research findings about 1,2,4-Butanetriol.

Reference:
Article; Xu, Qing-Song; Li, Chen; Xu, Yong; Xu, Defeng; Shen, Mei-Hua; Xu, Hua-Dong; Chinese Chemical Letters; (2019);,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 2568-33-4, Adding some certain compound to certain chemical reactions, such as: 2568-33-4, name is 3-Methylbutane-1,3-diol,molecular formula is C5H12O2, 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 2568-33-4.

A 50 mL three-necked flask that had been equipped with a column fitted with a side tube and packed with 20 g of molecular sieve (4A), a condenser, a thermometer and a drying tube was loaded with 0.64 g (2 mmol) of N, N?-bis(salicylidene)ethylenediamine iron (II), 1.04 g (10 mmol) of isoprene glycol, 40 g (400 mmol) of methyl methacrylate, 0.08 g of phenothiazine and 0.2 g of tridecane. While performing stirring at atmospheric pressure, the flask was placed into an oil bath set at 120 C. so that the temperature inside the flask would be 100 to 105 C. The reaction was performed for 11 hours while totally refluxing the distilled fraction back to the reaction system through the molecular sieve. The reaction liquid was sampled at prescribed lapses of time from the start of the reaction (3 hours, 5 hours, 7 hours, 9 hours and 11 hours). The gelation of the samples of the reaction liquid was evaluated as described in Test Example 3, the results being described in Table 1.

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. 2568-33-4, 3-Methylbutane-1,3-diol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KURARAY CO., LTD.; TAKAHATA, Yusuke; KAJIYASHIKI, Tsuyoshi; (9 pag.)US2018/50975; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 33420-52-9, 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. 33420-52-9, name is 2,2-Difluoropropan-1-ol. A new synthetic method of this compound is introduced below.

G. (R)-3-[N-(5′-Chloro-2′-fluoro-iphenyl-4-ylmethyl)-N’-oxalylhydrazino]-2-hydroxypropionic Acid 2,2-Difluoropropyl Ester (R)-3-[N’-t-Butoxyoxalyl-N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]2-hydroxy-propionic acid (15.0 mg, 32 mumol) was combined with HOBt (26.0 mg, 193 mumol) and EDC (34 muL, 0.2 mmol) in DCM (0.2 mL, 4 mmol). The solution was stirred for 10 minutes and 2,2-difluoropropanol (24.7 mg, 257 mumol) was added. The reaction was stirred at room temperature and monitored for completion. After 2 hours, the mixture was concentrated by rotary evaporation and the solvent was removed in vacuo. The resulting residue was dissolved in DCM (124 muL, 1.9 mmol). TFA (124 muL, 1.6 mmol) was added, and the resulting mixture was stirred for 2 hours. The solvent was removed in vacuo and the residue was purified by preparative HPLC to yield the title compound (2.2 mg). MS m/z [M+H]+ calc’d for C21H2O ClF3N2O6, 489.10; found 489.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33420-52-9, 2,2-Difluoropropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; HUGHES, Adam D.; FENSTER, Erik; FLEURY, Melissa; GENDRON, Roland; US2013/109639; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 83647-43-2, 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 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

(3-Bromo-2-methylphenyl)methanol (24 g, 119 mmol) was dissolved in dichloromethane (240 mL) and manganese (IV) oxide (103 g, 1.2 mol) was added. After stirring overnight, TLC showed no starting material. Reaction mixture was evaporated with silica gel and loaded on a small silica gel column. The product was eluted with hexane:ethyl acetate (10:1) to afford the pure aldehyde 3-bromo-2-methylbenzaldehyde (18.6 g) after evaporation. 1H NMR (600 MHz, CDCl3): 10.25 (s, 1H), 7.78 (m, 2H), 7.23 (t, 1H, J=7.7Hz), 2.75 (s, 3H). 13C NMR (150 MHz, CDCl3): 191.84, 137.72, 130.93, 130.20, 127.61, 127.37, 126.82, 18.13.

According to the analysis of related databases, 83647-43-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; KURA ONCOLOGY, INC.; GREMBECKA, Jolanta; CIERPICKI, Tomasz; BORKIN, Dmitry; POLLOCK, Jonathan; MIAO, Hongzhi; SUN, Duxin; LI, Liansheng; WU, Tao; FENG, Jun; REN, Pingda; LIU, Yi; (317 pag.)WO2016/40330; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 2854-16-2, 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. 2854-16-2, name is 1-Amino-2-methylpropan-2-ol. A new synthetic method of this compound is introduced below.

To a suspension of starting material C-1 b (13.5 g, 95.5 mmol) and K2C03 (19.8 g, 143.2 mmol, 1.5 eq.) in DMF (250 mL) is added amine D-1a (10.21 g, 114.5 mmol, 1.2 eq.) in one portion and stirred at 20 C for 16 h. The solvent is evaporated under reduced pressure and the residue is taken up in 100 mL water. The mixture is extracted with ethyl acetate (3 x 50 mL) and the combined organic layers are dried over MgS04 and filtrated. The organic solvent is evaporated under reduced pressure and the crude product is purified using normal phase chromatography (hexane/EtOAc 70:30) to afford pure product E-1a (yield: 95 % – 19.1 g, 90.5 mmol; HPLC-MS: (M+H)+ = 21 1 , tRet. = 0.9 min, method LCMSBAS).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2854-16-2, 1-Amino-2-methylpropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOESE, Dietrich; DAHMANN, Georg; ENGELHARDT, Harald; PETRONCZKI, Mark; SCHARN, Dirk; (0 pag.)WO2019/162323; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 109240-30-4, 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. 109240-30-4, name is 1-(4-Bromophenyl)cyclopropanol. A new synthetic method of this compound is introduced below.

General procedure: An argon-degassed solution of cyclopropanol 1 (2 equiv) in t-BuOH (0.0625 M) was added dropwise over 3 h to an argondegassed,stirred solution of acrylamide 4 (1 equiv) and manganese(III) acetylacetonate (2.2 equiv) in t-BuOH (0.114 M) at 26C. The resulting solution (0.03 M with respect to the cyclopropanol)was stirred for an additional 5 min before the solventwas removed under reduced pressure and the resulting residuepurified by flash chromatography to yield the desired oxindole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109240-30-4, its application will become more common.

Reference:
Article; Davis, Dexter C.; Haskins, Christopher W.; Dai, Mingji; Synlett; vol. 28; 8; (2017); p. 913 – 918;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 2867-59-6, 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. 2867-59-6, name is 3-Aminobutan-1-ol, molecular formula is C4H11NO, 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 3-aminobutan-1 -ol (500 mg, 5.61 mmol, 1 eq) in anhydrous DCM (25 ml_), cata- lytic amount of DMF (43 mI_, 0.56 mmol, 0.1 eq) was added, followed by dropwise addition of thionyl chloride (610 mI_, 8.414 mmol, 1.5 eq). The reaction was carried out 40C for 1 h, and continued at rt for further 16 h. The solvents were removed in vacuo. The residue was triturated using Et2Patent; RYVU THERAPEUTICS S.A.; DOBRZANSKA, Monika Patrycja; ZAWADZKA, Magdalena Izabela; RADZIMIERSKI, Adam; TOPOLNICKI, Grzegorz Witold; CWIERTNIA, Grzegorz Wojciech; MAHAJAN, Tushar Ravindra; FABRITIUS, Charles-Henry; CHMIELEWSKI, Stefan; GLUZA, Karolina Maria; ALVAREZ, Jose; ROGACKI, Maciej Krzysztof; MROCZKOWSKA, Magdalena; (215 pag.)WO2019/238786; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 6282-88-8, name is 3-(4-Chlorophenyl)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. name: 3-(4-Chlorophenyl)propan-1-ol

3- (4-chlorophenyl) propanol (17.1g, 0.1mol) was added to DMF (150ml) added successively N- (3- chloropropyl) piperidine (17.8g, 0.11mol), potassium carbonate (6.9g, 0.05mol), potassium iodide 1g, was heated to 95 , the reaction was stirred for 12 hours.The mixture was cooled to room temperature, then diluted with 300ml water, extracted twice with 400ml of ethyl acetate, the combined organic phases, 2N sodium hydroxide and twice with brine, dried over magnesium sulfate, filtered, and HCl at room temperature gas, stirring the precipitated solid was filtered and dried to give light yellow solid solution of 29.8 g, yield 89.7%, HPLC: 99.6%.

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, 6282-88-8, 3-(4-Chlorophenyl)propan-1-ol.

Reference:
Patent; Reyoung Pharmaceutical Co.,Ltd; Hu, qingwen; Cai, lianhui; Cao, Yan; Yu, zhibo; (7 pag.)CN104447620; (2016); B;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 5259-98-3 , The common heterocyclic compound, 5259-98-3, name is 5-Chloropentan-1-ol, molecular formula is C5H11ClO, 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.

Synthesis of Compound 13 To a solution of 5-chloro-l-pentanol (3.0 g, 24.47 mmol) Compound 11 in DMF (20 mL) was added sodium azide (1.909 g, 29.4 mmol) Compound 12. After being stirred at 60 ¡ãC for overnight, the reaction mixture was concentrated in vacu. The residue was purified by silica gel chromatography (EtOAc/Hexane 1 :3), to give product Compound 13 as clear liquid. 1H NMR (500 MHz, CDC13) delta 3.62 (m, 2H), 3.25 (t, J= 6.9 Hz, 2H), 1.63-1.53 (m, 4H), 1.45-1.40 (m, 2H).

The synthetic route of 5259-98-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TELLERS, David; COLLETTI, Steven, L.; DUDKIN, Vadim; AARONSON, Jeffrey; MOMOSE, Aaron; TUCKER, Thomas, Joseph; YUAN, Yu; CALATI, Kathleen, B.; TIAN, Lu; PARMAR, Rubina, G.; SHAW, Anthony, W.; WANG, Weimin; STORR, Rachel, Anne; BUSUEK, Marina; KOWTONIUK, Robert, A.; WO2013/166155; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts