Category: alcohols-buliding-blocks

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. 18068-06-9, name is 4-Methoxycyclohexanol. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 18068-06-9

The residue was dissolved in DCM (2.0 ml_), cooled to 0 C under nitrogen atmosphere, and then methanesulfonyl chloride (0.18 ml_, 2.39 mmol) and triethylamine (0.42 ml_, 2.98 mmol) were added succesively. The reaction mixture was stirred at 0 C for 1 h, and then quenched with water (20 ml_). The aqueous layer was extracted with DCM (3 x 10 ml_). The organic extracts were combined, filtered over a hydrophobic fit and concentrated under reduced pressure to provide (4- methoxycyclohexyl) methanesulfonate (320 mg, 1 .55 mmol, 78% yield) as a yellow oil.

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, 18068-06-9, 4-Methoxycyclohexanol.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (191 pag.)WO2017/46604; (2017); A1;,
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Electric Literature of 111-46-6, 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. 111-46-6, name is 2,2′-Oxybis(ethan-1-ol), molecular formula is C4H10O3, 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 2-(2-hydroxyethoxy)ethanol (55.66 g, 524.53 mmol, 49.70 mL, 2 eq) in tetrahydrofuran (500 mL) was added sodium hydride (6.29 g, 157.27 mmol, 60% purity, 0.6 eq) at 0 C and stirred for 0.5 hour under nitrogen. Then the mixture was added p- toluenesulfonyl chloride (50 g, 262.26 mmol, 1 eq), warmed to 25 C and stirred for 6 hours. The mixture was poured into saturated ammonium chloride solution (200 mL) and stirred for 15 minutes. The aqueous phase was extracted with ethyl acetate (200 mL x 2). The combined organic phase was washed with brine (200 mL), dried with anhydrous anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=l0/l to 1/1) to afford 2-(2-hydroxyethoxy)ethyl 4- methylbenzenesulfonate (35 g, 134.46 mmol, 51 % yield) as a yellow oil. LC/MS (ESI) m/z. 261.0 [M+l] +; 1H-NMR (400MHz, CDCb) d 7.76 – 7.72 (m, 2H), 7.28 (d, / = 8.0 Hz, 2H), 4.15 – 4.02 (m, 2H), 3.66 – 3.55 (m, 4H), 3.49 – 3.44 (m, 2H), 2.38 (s, 3H).

According to the analysis of related databases, 111-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARVINAS OPERATIONS, INC.; YALE UNIVERSITY; CREW, Andrew P.; HORNBERGER, Keith R.; WANG, Jing; DONG, Hanqing; BERLIN, Michael; CREWS, Craig M.; (1213 pag.)WO2019/195609; (2019); A2;,
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Electric Literature of 61439-59-6, 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. 61439-59-6, name is 2-(4-(Benzyloxy)phenyl)ethanol. A new synthetic method of this compound is introduced below.

Take 10.0 mL ionic liquid [Emim] [OSO2OE],Add 1.0 g (4.1 mmol) 4-phenoxyphenylethanol and 2.4 g (4.9 mmol) 2,3,4,6-tetra-O-acetyl-?[-0-glucopyranose trichloroacetimidate ,Nitrogen gas three times,Cool to 0 ° C,75 muL of TMSOTf (0.4 mmol) was added dropwise using a microsyringe.Keep the temperature at around 0 °C for about 0.5 hours.Then slowly increase to room temperature for 2 h.TLC detects the disappearance of alcohol raw materials,The reaction was quenched with triethylamine.The reaction solution was extracted with anhydrous diethyl ether to give the resulting glycoside.Combine the ether phase,Use a small amount of 4percent Na2CO3,Washed with saturated saline,Then add 4percent Na2SO4 to dry,The ether was removed by rotary evaporation and recrystallized from ethanol-cyclohexane to give 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-tetra-O-acetyl)-alpha-D-pyridin Glucosinolate1.83 g, milky white solid product, yield 80.1percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,61439-59-6, its application will become more common.

Reference:
Patent; Zaozhuang College; Zhou Fengyan; Zhang Wenzhi; Kong Xiaoyu; Yuan Yaru; Li Suwan; (12 pag.)CN107880085; (2018); A;,
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Electric Literature of 558-42-9 , The common heterocyclic compound, 558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, 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 3-bromo-5-fluoro-phenol (9.0 g, 47 mmol), and 1-chloro-2-methyl-propan-2-ol (5.116 g, 47.12 mmol), aqueous sodium hydroxide (37.69 g, 94.24 mmol) was added and the reaction mixture was heated at 120° C. for 5 days in a pressure vessel. The reaction was cooled and then extracted three times with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified on 220 g of silica gel utilizing a gradient of 0 to 10percent ethyl acetate in dichloromethane. The impure product was repurified on 220 g of gold silica gel utilizing a gradient of 0 to 10percent ethyl acetate in dichloromethane to yield 1-(3-bromo-5-fluoro-phenoxy)-2-methyl-propan-2-ol (4.75 g, 18.0 mmol, 38percent). ESI-MS m/z calc. 262.00046. found 263.0 (M+1)+. Retention time: 1.57 minutes (3 min run).

The synthetic route of 558-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
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Electric Literature of 6153-05-5, Adding some certain compound to certain chemical reactions, such as: 6153-05-5, name is (Z)-3-Methylpent-2-en-4-yn-1-ol,molecular formula is C6H8O, 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 6153-05-5.

n-BuLi (4.2 mL, 10 mmol, 2.4 mol/L) was added dropwise to a solution of (Z)-3-methylpent-2-en-4-yn-1-ol (0.48 g, 5 mmol) in THF (10 mL) at ?78 °C under a N2 atmosphere, and then the mixturewas stirred for 1 h at ?78 °C. A solution of 4g (0.94 g, 5 mmol) in THF (5 mL) was added slowly, themixture was stirred for 0.5 h at ?78 °C, and then it was warmed to room temperature and stirred for 2 h.The reaction was quenched with saturated aqueous NH4Cl solution (10 mL) and extracted with EtOAc(3 × 30 mL). The combined organics were washed with brine (2 × 20 mL), dried over anhydrousNa2SO4 and concentrated. The residue was purified by silica gel column chromatography (petroleumether/EtOAc, 1:2) to afford 6c (1.35 g, 95percent) as a yellow oil.

According to the analysis of related databases, 6153-05-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Xiaoqiang; Wan, Chuan; Yang, Dongyan; Yuan, Xiaoyong; Du, Shijie; Xiao, Yumei; Qin, Zhaohai; Molecules; vol. 18; 9; (2013); p. 10776 – 10788;,
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Reference of 24006-92-6, Adding some certain compound to certain chemical reactions, such as: 24006-92-6, name is (4,5-Dichloro-1,2-phenylene)dimethanol,molecular formula is C8H8Cl2O2, 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 24006-92-6.

Into a 100-mL round-bottom flask, was placed a solution of (4,5-dichloro-1,2-phenylene)dimethanol (500 mg, 2.41 mmol, 1.00 equiv) in dichloromethane (50 mL) and tribromophosphane (1.30 g, 4.80 mmol, 2.00 equiv). The resulting solution was stirred overnight at room temperature. The mixture was poured into 50 mL of water/ice. The resulting solution was extracted with 3×100 mL of ethyl acetate, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). The collected fraction was concentrated under vacuum to give 1,2-bis(bromomethyl)-4,5-dichlorobenzene (400 mg, 50%) as off-white oil. 1H-NMR (CDCl3, 4001411z, ppm): delta 7.48 (s, 2H), 4.57 (s, 4H).

According to the analysis of related databases, 24006-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Forma Therapeutics, Inc.; Bair, Kenneth W; Barczak, Nicholas; Han, Bingsong; Lancia, JR., David R.; Liu, Cuixian; Martin, Matthew W; Ng, Pui Yee; Rudnitskaya, Aleksandra; Thomason, Jennifer R; Zablocki, Mary Margaret; Zheng, Xiaozhang; (195 pag.)US2016/264518; (2016); A1;,
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Synthetic Route of 101597-25-5, 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.101597-25-5, name is 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, molecular formula is C17H16O3, molecular weight is 268.31, as common compound, the synthetic route is as follows.

2-Phenylthio-1,4-dihydroxynaphthalene (2 g) from Step 1 and 1,1-bis(4-methoxyphenyl)-2-propyn-1-ol (2.25 g) from Step 2 of Example 1 were added to a reaction flask containing 70 ml of toluene and stirred at room temperature. A catalytic amount of p-toluenesulfonic acid (about 100 mg) was added and stirred for 4 hours under a nitrogen atmosphere. Afterwards, the reaction mixture was poured into 50 ml of 10 weight percent aqueous sodium hydroxide solution. The organic layer was separated, washed and dried over anhydrous sodium sulfate. Evaporation of solvent resulted in an oily product which was purified using a silica gel column and a 1:1 mixture of chloroform:hexane as the eluant. The photochromic fractions were combined and the eluant was removed under vacuum. The resulting product was induced to crystallize from diethyl ether. The recovered product (2.5 g) had a melting point of 152-154C. A nuclear magnetic resonance (NMR) spectrum showed the product to have a structure consistent with 2,2-bis(4-methoxyphenyl)-5-phenylthio-6-hydroxy-2H-naphtho[1,2-b]pyran.

Statistics shows that 101597-25-5 is playing an increasingly important role. we look forward to future research findings about 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol.

Reference:
Patent; TRANSITIONS OPTICAL, INC.; EP994871; (2006); B1;,
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Electric Literature of 764-48-7, 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 764-48-7, name is Ethylene Glycol Vinyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A dry and argon-flushed 10 mL Schlenk tube, equipped with a stirring bar and septum, wascharged with 2-(vinyloxy)ethanol (5, 132 mg, 1.50 mmol, 1.50 equiv) in Et2O (1.5 mL). Then,iPrMgBr (1.55 mmol, 1.55 equiv) was added dropwise at 25 C. After 5 min of stirring,Sc(OTf)3 (49.2 mg, 0.10 mmol, 0.10 equiv) and aldehyde 6 (1.00 mmol, 1.00 equiv) weresuccessively added and the reaction mixture was stirred at 40 C for the given time. After afull conversion was detected by GC-analysis, sat. aq. NH4Cl (15 mL) was added and theaqueous layer was extracted with EtOAc (3 x 15 mL). The combined organic layers weredried over Na2SO4, filtered and solvent was removed under reduced pressure. Purification viacolumn chromatography (SiO2) afforded expected products 4.

According to the analysis of related databases, 764-48-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Quinio, Pauline; Kohout, Laura; Roman, Daniela Sustac; Gaar, Jakob; Karaghiosoff, Konstantin; Knochel, Paul; Synlett; vol. 27; 11; (2016); p. 1715 – 1719;,
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Adding a certain compound to certain chemical reactions, such as: 2867-59-6, 3-Aminobutan-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, 2867-59-6, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C4H11NO

6-(4-Chlorophenyl)-2-(3-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (70 mg, 0.20 mmol) was dissolved in anhydrous DMF (1.5 mL). (3RS)-3-Aminobutan-1 -ol (36.2 mg, 0.41 mmol), N-ethyl-N-isopropylpropan-2-amine (0.159 mL, 0.91 mmol), and propane phosphonic acid anhydride (T3P, 178 mu, 50% in DMF, 305mueta-iotaomicronIota) were successively added. It was stirred at rt overnight. The crude reaction mixture was purified by RP-HPLC (column: X-Bridge C18 5muetaiota 100x30mm, mobile phase: (water + 0.2 vol% aqueous ammonia (32%)) / acetonitrile, gradient) to yield 47 mg (56%) of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm] = 1 .19 (d, 3H), 1.59 – 1 .74 (m, 2H), 3.48 (t, 2H), 4.08 – 4.20 (m, 1 H), 4.50 (br s, 1 H), 7.34 – 7.42 (m, 1 H), 7.52 – 7.66 (m, 5H), 7.96 – 8.03 (m, 2H), 8.63 (s, 1 H), 9.31 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2867-59-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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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, Safety of 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, blongs to alcohols-buliding-blocks compound. Safety of 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol

A 500 mL three-necked flask equipped with a water trap was charged with 1-hydroxypyrene (Ea0,623 mg, 2.85 mmol), a propargyl alcohol derivative (E0, 903 mg, 3.36 mmol)3.5g of acidic alumina and 300mL of toluene, under argon protection, dark reaction 90 C for 35h, the solution was dark green.After cooling to room temperature, the reaction mixture was suction filtered, the filter cake was washed with dichloromethane, the filtrate and the washings were combined, the solvent was spin dried,The crude product was separated by column chromatography, and the resulting crude product was recrystallized from absolute ethanol to give 210 mg of a light yellow solid in a yield of 22%. Yield 55%.

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:
Patent; Shanghai Gantian Optical Materials Co., Ltd.; Gan Jiaan; (9 pag.)CN104016996; (2017); B;,
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