Month: February 2021

Synthetic Route of 395-23-3, 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. 395-23-3, name is Phenyl(4-(trifluoromethyl)phenyl)methanol. A new synthetic method of this compound is introduced below.

Example 171: l-(4-Fluorophenyl)-3-(phenyl(4-(trifluoromethyl)phi methyl)ureaStep 1. Phenyl(4-(trifluoromethyl)phenyl)methanoneA solution of 4-(trifluoromethyl)benzhydrol (1.836 g, 7.3 mmol) in anhydrous DCM (65 mL) was treated with manganese(IV) oxide (<5 micron, activated) (5.7 g, 66 mmol). The resulting suspension was stirred at rt for 12 days. The catalyst was removed by filtration through a Celite brand filter agent pad. The filtrate was concentrated, and the resulting solid was dried under high vacuum to afford the title compound as a white solid. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,395-23-3, its application will become more common. Reference:
Patent; AMGEN INC.; BROWN, James; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; LIU, Qingyian; MONENSCHEIN, Holger; NGUYEN, Thomas T.; NISHIMURA, Nobuko; ZHONG, Wenge; WO2012/177896; (2012); A1;,
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Reference of 111-90-0, 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 111-90-0, name is Diethylene Glycol Monoethyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of DCM, diethylene glycol mono ethyl ether (21.0 ml_, 150 mmol), and triethylamine (34.7 ml_, 250 mmol) under a nitrogen atmosphere at -78 0C was added dropwise bromo acetyl bromide (17.2 ml_, 200 mmol). After stirring at -78 0C for 3 h, the reaction mixture was allowed to warm up to -20 0C and quenched by addition of water (50 ml_). The organic phase was washed with distilled water (3 x 50 ml_), saturated ammonium chloride (3 x 50 ml_), saturated sodium bicarbonate (3 x 50 ml_) and brine (2 x 50 ml_). The organic phase was then dried over magnesium sulfate, filtered and solvents removed via rotary evaporation to yield a crude product in 87 % yield. This crude product was distilled (bp 105 – 115 0C) to give a colourless liquid at RT in 71 % yield.

According to the analysis of related databases, 111-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DUBLIN CITY UNIVERSITY; WO2009/24607; (2009); A1;,
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Electric Literature of 402-63-1, 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. 402-63-1, name is 1-(3-Fluorophenyl)ethanol. A new synthetic method of this compound is introduced below.

Example 100 1-(3-Fluorophenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (99 mg) was added to toluene/triethylamine = 10/1 (10 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (150 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-fluoro-alpha-methylbenzyl alcohol (70 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (60 mg, yield 36%). 1H-NMR (CDCl3, 400 MHz): 8.75 (1H, s), 7.98 (1H, bs), 8.47 (1H, bs), 6.48 – 7.60 (9H, m), 5.82 – 5.90 (1H, m), 4.13 (3H, s), 4.08 (3H, s), 1.58 (3H, d, J = 6.6 Hz) Mass spectrometry value (ESI-MS, m/z): 464 (M++1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,402-63-1, 1-(3-Fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1243582; (2002); A1;,
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Synthetic Route of 931-17-9, 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. 931-17-9, name is 1,2-Cyclohexanediol. A new synthetic method of this compound is introduced below.

EXAMPLE 77a Preparation of intermediate cyclopent-1-enecarbaldehyde To an acidic solution of sodium periodate (28.3 g, 0.13 mol) (Aldrich) in water (250 mL) was added the solution of 1,2-cycohexanediol (12 g, 0.10 mol) (Acros) in ethyl ether (150 mL). The mixture was stirred vigorously for 0.5 h at room temperature. After addition of KOH aqueous solution (20%, 38.4 mL), the reaction mixture was stirred for an additional 1 h. The mixture was extracted with ethyl ether. The organic layers were combined and dried. The solvent was removed to give cyclopent-1-enecarbaldehyde as yellow oil (Yield: 7.2 g, 75%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,931-17-9, 1,2-Cyclohexanediol, and friends who are interested can also refer to it.

Reference:
Patent; Chen, Li; Ding, Qingjie; Liu, Jin-Jun; Yang, Song; Zhang, Zhuming; US2007/213341; (2007); A1;,
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Reference of 702-82-9 ,Some common heterocyclic compound, 702-82-9, molecular formula is C10H17NO, 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.

A solution of 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylic acid (18, 3.08 mmol) obtained in the step 4) -dimethylaminopropyl) -3-ethylcarbodiimide (1.182 g, 6.18 mmol), 4-dimethylaminopyridine (0.3858, 3.08 mmol), 1-hydroxybenzotriazole (0.4158, 3.08 mmol ), 3-hydroxyamantanamine (4.62 mmol) and mixing to give a mixture I; sealing the vessel in which said mixture I is located, evacuating, passing nitrogen;After repeating the above steps three times, tetrahydrofuran and dimethylformamide were added to the mixture I under a nitrogen atmosphere to obtain a mixture; the tetrahydrofuran and TN, N-dimethylformamide were both dried and anhydrous ; Heating the mixture to a temperature of 40 C and heating for 6 hours, extracting, washing with water, combining and showing signs of drying to the mixture K; the extraction is carried out using a mixture of ethyl acetate Ester extraction, and the extraction process was repeated three times; the water washing process was repeated twice; and the drying was carried out using anhydrous sodium sulfate. The mixture K is subjected to distillation under reduced pressure to precipitate a solid; and the precipitated solid is filtered and washed to obtain a product. The washing was carried out using a mixed solution of ethyl acetate and n-hexane.

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. 702-82-9, 3-Aminoadamantan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chongqing Medical College; SHI, LEI; NIU, YA HUI; (10 pag.)CN105884783; (2016); A;,
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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.14320-38-8, name is Cyclopent-3-enol, molecular formula is C5H8O, molecular weight is 84.12, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

To an ice-cooled solution of 4-hydroxycyclopentene (50.0 g, 0.594 mol) and imidazole (80.9 g, 1.19 mol) in N,N-dimethylformamide (300 mL) was slowly added tert-butyldiphenylsilyl chloride (180 g, 0.65 mmol). The reaction mixture was warmed toroom temperature. After 16 h, the reaction mixture was diluted with water (1 L) and ethyl acetate (500 mL). The aqueous layer was extracted with ethyl acetate (2 x 200 mL). The combined organics were washed sequentially with water (3 x 300 mL) and saturated aqueous sodium chloride solution (2 x 200 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography(15:1 petroleum ether / ethyl acetate) providedtert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane (188 g, 98 %) as a colorless oil. 1H NMR (400 MHz, CDC13): oe: 7.69 – 7.66 (m, 4H), 7.43 – 7.38 (m, 6H), 5.63 – 5.60 (m, 2H), 4.58 – 4.53 (m, 1H), 2.46 – 2.38 (m, 4H), 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14320-38-8, Cyclopent-3-enol, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
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Synthetic Route of 41175-50-2 , The common heterocyclic compound, 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, molecular formula is C12H15NO, 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.

In a screw-cap bottle, 8-hydroxyjulolidine 10 (0.60 g, 3.17 mmol) and trimellitic anhydride 11 (1.83 g, 9.51 mmol) were suspended in acetic acid (15 mL) and flushed with argon. Cone. H2 S O4 (1 drop) was added, and the reaction mixture was gradually heated in an oil bath (up to 100 C) and stirred for 2.5 h. The precipitate dissolved at about 80-90 C, and a red solution formed. After about 0.5 h, a “new” precipitate was formed. After cooling to room temperature, the purple suspension was transferred into centrifuge test-tubes, sonicated for several seconds in an ultrasonic bath, centrifuged, and the purple supernatant solution was discarded. The precipitate was washed with acetic acid (5 mL) ; the same sonication centrifugation cycles were repeated 5 – 6 times, until the supernatant solution became colorless. The solid residue was dried in vacuo to obtain 0.48 g (40%) of benzophenone 12a with traces of 12b (>95:<5). Beige solid; TLC: ACN/H20/DCM, 9:1:1. HPLC (Eurospher-100 C18 5 pm 250x4 mm, 1.2 mL/min; solvent A: water + 0.1% v/v trifluoroacetic acid (TFA) ; solvent B: MeCN + 0.1% v/v TFA). A/B: 30/70 - 100/0, 25 min, tR = 9.7 min (12a), 10.7 min (12b). NMR (400 MHz, DMSO-d6) delta 12.82 (s, 1H) , 8.09 (0228) (dd, J = 8.1, 1.7 Hz, 1H) , 8.02 (d, J = 8.1 Hz, 1H) , 7.76 (d, J = 1.7 Hz, 1H) , 6.39 (s, 1H) , 3.24 (td, J = 7.4, 4.8 Hz, 4H) , 2.58 (t, J = 6.4 Hz, 2H) , 2.40 (t, J = 6.2 Hz, 2H) , 1.91-1.78 (0229) (m, 2H) , 1.80-1.69 (m, 2H) . C2iHi9N06 (381.12124). MS (ESI): ml z (0230) (negative mode, %) = 380 (100) [M-H]-. The synthetic route of 41175-50-2 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E. V.; BUTKEVICH, Alexey; BELOV, Vladimir N.; HELL, Stefan W.; KAMIN, Dirk; SIDENSTEIN, Sven; SHOJAEI, Heydar; KOLMAKOV, Kirill; SOKOLOV, Viktor V.; (116 pag.)WO2018/46753; (2018); A1;,
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Application 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.

To a mixture of 2-(4-benzyloxyphenyl)ethanol (1.19 g), triethylamine (700 mg), and ethyl acetate (30 ml), methanesulfonyl chloride (790 mg) was added dropwise at 0¡ãC, and the mixture was stirred at room temperature for two hours. The reaction mixture was washed with water, saturated aqueous sodium bicarbonate solution, 1 N hydrochloric acid, then, with saturated sodium chloride solution, and dried (MgSO4) and concentrated. To a mixture of the residue, ethyl (3-phenyl-1H-pyrazol-4-yl)acetate (1.0 g), and N, N-dimethylformamide (50 ml), sodium hydride (60percent, oily, 190 mg) was added at 0¡ãC, and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl [1-[2-(4-benzyloxyphenyl)ethyl]-3-phenyl-1H-pyrazol-4-yl]acetate (0.45 g, yield: 24percent) was obtained as a colorless oily substance in the fraction eluted with diethyl ether-hexane (2:3, volume ratio). NMR(CDCl3) delta : 1.22(3H, t, J=7.0 Hz), 3.15(2H, t, J=7.4 Hz), 3.57(2H, s), 4.13(2H, q, J=7.0 Hz), 4.31(2H, t, J=7.4 Hz), 5.05(2H, s), 6.87-6.92(2H, m), 7.02-7.07(2H, m), 7.31-7.47(9H, m), 7.58-7.64(2H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61439-59-6, 2-(4-(Benzyloxy)phenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1228067; (2004); B1;,
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Related Products of 111-90-0, 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. 111-90-0, name is Diethylene Glycol Monoethyl Ether. A new synthetic method of this compound is introduced below.

In a round bottom flask NaH (3.9 g, 0.163 mol) was dispersed in 150 ml of anhydrous THF. Anhydrous di(ethylene glycol) ethyl ether (20 g, 0.149 mol) was dissolved in THF (50 ml) and added dropwise to the NaH suspension. The reaction mixture was stirred for 2 hours. The solution of ethyl 3-bromopropionate (17.5 ml, 0.140 mol) in THF (20 ml) was added to a pre-cooled reaction mixture (t=-10 C.). The reaction mixture was stirred overnight, and the solvent was evaporated completely. [00150] Ethylacetate was added to the residue and a mixture was washed with a solution of 10% NaCl and deionized water. The ethylacetate solution was dried over MgSO4, filtered, and the solvent was evaporated. The residue was dried using a vacuum pump. The crude material was chromatographed on a silica gel column. Fractions containing the Compound III were collected, concentrated and characterized by TLC, HPLC, MS and NMR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111-90-0, its application will become more common.

Reference:
Patent; Nobex Corporation; US6713454; (2004); B1;,
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Electric Literature of 6240-11-5, 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. 6240-11-5, name is 1-Adamantaneethanol. A new synthetic method of this compound is introduced below.

A. A mixture of 2-(adamant-1-yl)ethanol (2.1 g, 12 mmoles), disuccinimidyl carbonate (3.3 g, 13 mmoles) and pyridine (0.86 ml, 10 mmoles) in acetonitrile (50 ml) was stirred at room temperature for 24 hours, then the solvent was evaporated off in the cold and the residue was dissolved in methylene chloride (100 ml). The solution was washed with water (50 ml), 1N HCl (50 ml) and water again (50 ml). The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated off to give 3 g (9 mmoles) of crude 2-(adamant-1-yl)ethyl-succinimidyl carbonate which was redissolved in THF (30 ml).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6240-11-5, 1-Adamantaneethanol, and friends who are interested can also refer to it.

Reference:
Patent; Italfarmaco S.p.A.; US6034096; (2000); A;,
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