Category: alcohols-buliding-blocks

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. 112-70-9, name is 1-Tridecanol. A new synthetic method of this compound is introduced below., 112-70-9

General procedure: To a soln. of peracetyl beta-D-O-galactopyranoside 1 (1 equiv.) and the fatty alcohol (2-8, 2 equiv.) in dry MeCN (10 mL), was added BF3*Et2O (1 equiv.). This mixture was transferred into the microwave oven with rigorous stirring for 12 min at 120 C (ramp time: 10 min). Solvent was removed in vacuum, and the resulting residue was diluted with EtOAC and washed successively with sat. NaHCO3 and brine. The combined organic layer was dried over NaSO4, filtered, concentrated in vacuum to give a crude mixture residue which was separated by column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112-70-9, 1-Tridecanol, and friends who are interested can also refer to it.

Reference:
Article; Song, Shao-Xing; Wu, Ming-Li; He, Xiao-Peng; Zhou, Yu-Bo; Sheng, Li; Li, Jia; Chen, Guo-Rong; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2030 – 2032;,
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100-37-8, 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. 100-37-8, name is 2-(Diethylamino)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of N,N-diethylethanolamine (0.08 g, 0.7 mmol) (Aldrich) in DMF (5 mL) was added sodium hydride (0.028 g, 0.7 mmol). The mixture was stirred at room temperature for 30 minutes, and then 4-chloro-3-[(2-methanesulfonyl-7-oxo-7,8-dihydro-pyrido-pyrido[2,3-d]-pyrimidine-6-carbonyl)-amino]-benzoic acid methyl ester (0.044 g, 0.10 mmol) (from Example 32 supra) was added and the mixture was stirred at room temperature for 18 hours. The mixture was purified by HPLC eluting with MeCN/H2O to give 4-chloro-3-{[2-(2-diethylamino-ethoxy)-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl]-amino}-benzoic acid. (Yield 0.030 g, 65.2%).

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 100-37-8, 2-(Diethylamino)ethanol.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 346-06-5, (2-(Trifluoromethyl)phenyl)methanol, 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, 346-06-5, blongs to alcohols-buliding-blocks compound. 346-06-5

Polystyrene triphenylphoshine (9.84 g, 1.58 mmol/gram, 15.5 mmol) was stirred in 100 mL of [DICHLOROMETHANE] for ten minutes. The regioisomeric mixture of methyl [5- (6-] { [(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1H-benzimidazol-1-yl)-3-hydroxy-2- [THIOPHENECARBOXYLATE] and methyl [5- (5-] { [(1,1-dimethylethyl)-(diphenyl)silyl]oxy}-1H- [BENZIMIDAZOL-1-YL)-3-HYDROXY-2-THIOPHENECARBOXYLATE] (5.48 g, 10.4 mmol) was added in a single portion. 2-(Trifluromethyl)benzyl alcohol (1.68 mL, 12.6 mmol) was added via syringe, and the solution was cooled to [0] [OC.] [DI-TERT-BUTYL AZODICARBOXYLATE] (3.58 g, 15.5 mmol) was dissolved in 20 [ML OF DICHLOROMETHANE] and added dropwise via addition funnel. The reaction was warmed to room temperature and stirred for 1.5 hours. The mixture was filtered through filter paper, and the solid was washed with dichloromethane and methanol. The filtrate was concentrated and purified by flash chromatography to afford 2.89 g [(41percent)] of methyl 5-(5-{[(1, 1- dimethylethyl)(diphenyl)silyl]oxy}-1H-benzimidazol-1-yl)-3-({[2- [(TRIFLUOROMETHYL) PHENYL] METHYL} OXY)-2-THIOPHENECARBOXYLATE] and 2.69 g [(38percent)] of methyl [5- (6- { [ (1, 1-DIMETHYLETHYL) (DIPHENYL) SILYL] OXY}-1 H-BENZIMIDAZOL-1-YL)-3- ( { [2-] (trifluoromethyl)phenyl]methyl}oxy)-2-thiophenecarboxylate. Data for 5-OTBDPS regioisomer [:APOS;H] NMR (300 MHz, [DMSO-D6)] [8] 8.66 (s, 1 H), 7.98 (d, J = 7.6 Hz, 1 H), 7.86- 7.60 (m, 9H), 7.56-7. 44 (m, 6H), 7.01 (s, 1 H), 6.99 (dd, J = 6.7, 2.4 Hz, 1 H), 5.51 (s, 2H), 3.79 (s, 3H), 1.10 (s, 9H). MS [(ES+,] m/z) 687 [(M+1).] Data for 6-OTBDPS regioisomer: ‘H NMR (300 MHz, [DMSO-D6)] 8 8.60 (s, [1 H),] 7.99 (d, J= 7.6 Hz, [1 H),] 7.87-7. 57 (m, 9H), 7.54-7. 42 (m, 6H), 7.07 (d, J = 2.0 Hz, 1 H), 6.92 [(DD,] J = 8.8, 2.3 Hz, 1 H), 5.46 (s, 2H), 3.84 (s, [3H),] 1.11 (s, 9H). MS [(ES+,] m/z) 687 [(M+1).]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,346-06-5, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/14899; (2004); A1;,
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3597-91-9, 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. 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol, molecular formula is C13H12O, 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.

General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 ¡Á 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.

The chemical industry reduces the impact on the environment during synthesis 3597-91-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Khazdooz, Leila; Zarei, Amin; Aghaei, Hamidreza; Azizi, Ghobad; Gheisari, Mohammad Mehdi; Tetrahedron Letters; vol. 57; 2; (2016); p. 168 – 171;,
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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 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol. This compound has unique chemical properties. The synthetic route is as follows. 722-92-9

Step A: 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol To a stirred solution of copper(II) bromide (1.293 g, 5.79 mmol) in acetonitrile (15 mL) was added tert-butyl nitrite (0.764 mL, 5.79 mmol) in one portion at 60¡ã C. A solution of 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1 g, 3.86 mmol) in acetonitrile (3 mL) was then added dropwise at 60¡ã C. After stirring for 15 min at 60¡ã C., the mixture was concentrated. The residue was diluted with water (20 mL) and extracted with EtOAc (10 mL, 2*4 mL). The combined organic solutions were dried over anhydrous sodium sulfate and concentrated. Flash chromatography purification using (24 g silica gel column, gradient elution from 0 to 30percent of ethyl acetate in hexanes) afforded 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.3 g, 4.02 mmol, 104percent yield) as a liquid.

Statistics shows that 722-92-9 is playing an increasingly important role. we look forward to future research findings about 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol.

Reference:
Patent; Duan, Jingwu; Dhar, T. G. Murali; Jiang, Bin; Lu, Zhonghui; Xiao, Hai-Yun; US2015/191483; (2015); A1;,
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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. 27129-87-9, name is (3,5-Dimethylphenyl)methanol. A new synthetic method of this compound is introduced below., 27129-87-9

Compound Ba (2.5 g, 95%) was obtained as colorless crystals using Compound A (1.8 g) obtained in Reference Example 1, 3,5-dimethylbenzyl alcohol (1.7 mL), triphenylphosphine (3.0 g), diethyl azodicarboxylate (1.8 mL) and tetrahydrofuran (7.5 mL) as described in Example 14. [0458] 1H NMR (270 MHz, CDCl3) delta6.96 (1H, brs), 6.86 (2H, brs), 4.68 (2H, s), 4.17 (2H, q), 3.89 (2H, t), 3.65 (2H, dd), 3.42 (2H, dd), 2.79 (2H, t), 2.31 (6H, s), 1.28 (3H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,27129-87-9, (3,5-Dimethylphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; Kyowa Hakko Kogyo Co., Ltd.; US2003/225288; (2003); A1;,
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307353-32-8 ,Some common heterocyclic compound, 307353-32-8, molecular formula is C9H9BrO3, 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.

2-(Trifluoromethyl)phenyl)boronic acid (114 mg, 0.60 mmol), PdCl2(dppf) (12 mg, 0.016 mmol), Et3N (167 muL, 1.2 mmol) were added to a solution of methyl 3-bromo-5-(hydroxymethyl)benzoate (97.5 mg, 0.40 mmol) in EtOH (4 mL). The reaction mixture was stirred at 85 C. overnight, diluted with EtOAc and washed with water. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (Combi-flash Rf, Hex/EtOAc=0-60% gradient) to afford the title compound (100 mg, 80%). 1H NMR (400 MHz, CDCl3) delta 8.09 (s, 1H), 7.95 (s, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.56 (m, 3H), 7.33 (d, J=7.6 Hz, 1H), 4.81 (d, J=6.0 Hz, 2H), 3.94 (s, 3H), 1.79 (t, J=6.0 Hz, 1H).

According to the analysis of related databases, 307353-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vanderbilt University; Alvarado, Joseph R.; Stauffer, Shaun R.; Gogliotti, Rocco D.; Han, Changho; Meyers, Kenneth M.; Tian, Jianhua; Macdonald, Jonathan D.; Fesik, Stephen W.; Lee, Taekyu; US2020/102288; (2020); A1;,
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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.722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, molecular weight is 259.15, as common compound, the synthetic route is as follows.722-92-9

A suspension of 2-(4-aminophenyl)-1 ,1 ,1 ,3,3,3-hexafluoro-2-propanol (1.0g), his-(2- chloroethyl)amine hydrochloride (0.69g) and potassium carbonate (0.53g) in 2- butoxyethanol (5ml), was heated at 180¡ã for 24 hours. Diluted with ethyl acetate and washed with saturated NaHCO3 solution and brine. Organic layer dried and evaporated to give crude product. Chromatography on silica gel gave, after elution with 0-20percent methanol in DCM, the desired product as a brown solid (0.54g). LC/MS (ESI) found 329 (M+H).

Statistics shows that 722-92-9 is playing an increasingly important role. we look forward to future research findings about 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/94842; (2006); A1;,
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33420-52-9, 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 33420-52-9 as follows.

To a stirred solution of 5-{9-fluoro-6-methanesulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-3-yl}-4-(2H3)methyl-1-methyl-1H-1,2,3-triazole (31.0 mg, 0.0600 mmol) and 2,2-difluoropropan-2-ol (27.8 mg, 0.290 mmol) in NMP (0.30 mL) was added t-BuOK (25.9 mg, 0.230 mmol). This mixture was heated at 65 C. for 1 h and cooled to room temperature. The mixture was diluted with MeOH and purified via preparative LC/MS with the following conditions: Column: Waters XBridge Phenyl, 19¡Á200 mm, 5-mum particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 15-70% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 5-[9-(2,2-difluoropropoxy)-6-methanesulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-3-yl]-4-(2H3)methyl-1-methyl-1H-1,2,3-triazole (13.8 mg, 37%). 1H NMR (500 MHz, DMSO-d6) delta 8.60 (s, 1H), 8.29 (d, J=8.8 Hz, 1H), 7.74 (s, 1H), 7.56 (br d, J=7.7 Hz, 2H), 7.36-7.29 (m, 2H), 7.28-7.22 (m, 1H), 7.18 (d, J=8.9 Hz, 1H), 6.74 (s, 1H), 4.67 (br t, J=12.0 Hz, 2H), 3.86 (br d, J=15.1 Hz, 1H), 3.73 (s, 3H), 3.60-3.55 (m, 1H), 3.49 (br t, J=11.5 Hz, 1H), 3.33 (br d, J=11.8 Hz, 1H), 3.23-3.16 (m, 1H), 2.54 (s, 3H), 1.95 (br t, J=19.4 Hz, 3H), 1.69 (br d, J=10.8 Hz, 1H), 1.62-1.50 (m, 1H), 1.22 (br d, J=8.8 Hz, 1H), 0.43 (br d, J=12.0 Hz, 1H). LCMS: RT=1.731 min; (ES): m/z (M+H)+=613.15, LCMS: Column: Waters Acquity UPLC BEH C18, 2.1¡Á50 mm, 1.7-mum particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10 mM ammonium acetate; Temperature: 50 C.; Gradient: 0-100% B over 3 min, then a 0.75-min hold at 100% B; Flow: 1.11 mL/min. HPLC Purity at 220 nm: 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Norris, Derek J.; Delucca, George V.; Gavai, Ashvinikumar V.; Quesnelle, Claude A.; Gill, Patrice; O’Malley, Daniel; Vaccaro, Wayne; Lee, Francis Y.; DeBenedetto, Mikkel V.; Degnan, Andrew P.; Fang, Haiquan; Hill, Matthew D.; Huang, Hong; Schmitz, William D.; Starrett, JR., John E.; Han, Wen-Ching; Tokarski, John S.; Mandal, Sunil Kumar; (220 pag.)US2016/176864; (2016); A1;,
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53066-19-6 , The common heterocyclic compound, 53066-19-6, name is 1-(2,6-Dichlorophenyl)ethanol, molecular formula is C8H8Cl2O, 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 solution of 1 -(2,6-dichlorophenyl)ethanol (9.0 g, 47.11 mmol) in THF (200 niL) at 0 C was added NaH (60% dispersion in mineral oil, 2.45 g, 61.24 mmol) inportions. When the evolution of gas bubble stopped, a solution of 3-fluoro-2-nitropyridine (6.69 g, 47.11 mmol) in THF (50 mL) was added to the system. The reaction was stirred at room temperature overnight, then quenched with H20 (10 mL) at 0 C, and concentrated in vacuo. The residue was diluted with H 0 (200 mL), and extracted with EtOAc (150 mL x 3). The combined organic phases were washed with saturated aqueous aHC03 (200 mL) followed by brine (200 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo to give the title compound as a brown solid (14.34g,97.2%).

According to the analysis of related databases, 53066-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
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