Month: August 2021

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.23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, molecular weight is 208.25, as common compound, the synthetic route is as follows.SDS of cas: 23783-42-8

A THF solution (200 mL) of H(OCH2CH2)4OMe (12 g, 60 mmol) and a stir bar was placed in a threenecked flask (500 mL). NaH (60%, dispersion in Paraffin Liquid, 2.9 g, 72 mmol) was added to the solution, and the mixture was stirred at room temperature for 30 min. Allyl bromide (6.2 mL, 72 mmol) was slowly added to the resulting mixture at the same temperature with vigorous stirring. The solution was stirred overnight, and the remaining NaH and NaBr were filtered off. The obtained filtrate was concentrated to dryness in vacuo. The residue was dissolved in water (500 mL) and extracted with hexane (200 mL3) and then dichloromethane (200 mL3). The resulting organic layer was dried with MgSO4 and then further dried under vacuum to afford the title compound 1d as a colorless oil (14 g, 55 mmol, 92%) 1d: 1H NMR (600 MHz, C6D6): delta 5.82 (m, CH2CHCH2O, 1H), 5.23 (m, CH2CHCH2O, 1H), 5.01 (m, CH2CHCH2O, 1H), 3.82 (m, CH2CHCH2O, 2H), 3.50-3.43 (m, CH2, 12H), 3.42-3.40 (m, CH2, 2H), 3.34 (m, CH2, 2H), 3.12 (s, OCH3, 3H). 13C{1H} NMR (150 MHz, C6D6): 135.7, 115.9, 72.4, 72.1, 71.07, 71.04 (3), 71.0, 70.9, 70.0, 58.6. HRMS (ESI): m/z calcd for [C12H24O5Na]+ (M+Na): 271.1516; found 271.1506.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Article; Inomata, Koya; Naganawa, Yuki; Guo, Haiqing; Sato, Kazuhiko; Nakajima, Yumiko; Tetrahedron Letters; vol. 60; 41; (2019);,
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Reference of 7397-62-8 ,Some common heterocyclic compound, 7397-62-8, molecular formula is C6H12O3, 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 3-neck, 50 mL flask (equipped with a thermocouple, magnetic stirrer, heating mantle, reflux condenser, and N2 purge) was added the intermediate (4) from Part B (1.0 g, 2.79 mmol), ethylene glycol (7.0 g), [1,] 8-diazabicyclo [5.4. 0] undec-7-ene (“DBU”, 42 mg, 0.28 mmol, 0.1 equivalents relative to the intermediate (4) ), and butyl glycolate (5) (1.1 g, 8. [38] mmol, 3.0 equivalents relative to the intermediate (4) ). The resulting white slurry was heated to [80C,] and then stirred at this temperature for 4.9 hr. Although the slurry initially formed a light yellow solution during this heating, it formed a clear solution after 40 min of heating. Following the 4.9 hr heating period, deionized water was added over a 15 min period in an amount such that the mixture became slightly turbid. During this water addition, the temperature was maintained at [80C.] The resulting mixture was stirred for another hour at this temperature, and then allowed to cool naturally to room temperature. The resulting precipitate was filtered, washed with water [(2X10] mL), and air-dried for 1.3 hr to afford 1.10 g of light yellow crystals. Liquid chromatography analysis comparing these crystals with a pre-formed standard indicated the formation of the desired product (6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7397-62-8, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2003/104223; (2003); A1;,
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Synthetic Route of 6850-65-3, 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. 6850-65-3, name is 4-Aminocyclohexan-1-ol(isomers mixture), molecular formula is C6H13NO, 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 procedures for the preparation of l,l-difluoro-4-isocyanocyclohexane F. p HCOOEt F-?^| O PPh3 p ” tauAlpha ” ^^N^H ” v ,N. H NC Step A: Tert-but l 4-hydrox cyclohexylcarbamate. To a solution of 4-aminocyclohexanol (23 g, 0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified by column chromatography on silica gel using DCM/ MeOH (V:V, 20: 1) to afford the desired product as a white solid. MS: 216.2 (M+l)+.

According to the analysis of related databases, 6850-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2013/107291; (2013); A1;,
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Reference 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.

In a 1 L round bottom flask equipped with a reflux condenser, 126.20 g (0.70 mol) of 2- (1-adamantyl) ethanol was added while 164 g of concentrated sulfuric acid and 200 g (48% aqueous solution) of hydrobromic acid were cooled in an ice bath, . The mixture was refluxed for 6 hours, cooled to room temperature and then added to 400 g of ice. The aqueous phase was extracted with 400 ml of pentane. The organic phase was washed with 2 M NaOH solution and water, dried over magnesium sulfate and the solvent was removed in vacuo. The product was distilled in vacuo to give 153.2 g (90%) of (1- (2-bromo-ethyl) -adamantane as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6240-11-5, its application will become more common.

Reference:
Patent; LUMMUS NOVOLEN TECHNOLOGY GMBH; (91 pag.)JP6196581; (2017); B2;,
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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.100-86-7, name is 2-Methyl-1-phenyl-2-propanol, molecular formula is C10H14O, molecular weight is 150.22, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

100.6 ml of concentrated sulfuric acid (9.4 eq.) are placed in a 500 ml three-necked flask equipped with a condenser and a thermometer, followed by cooling to a temperature in the region of 5- 10C. A mixture containing 30 g of methyl- 1 -phenyl-2-propanol (1 eq.) and 9.83 g of acetonitrile (1 eq.) is added dropwise. The mixture is stirred for 5 minutes at a temperature in the region of 5-10C and then for 5 hours at room temperature (monitoring by TLC, 95/5 CH2Cl2/MeOH). (0210) The mixture is then poured into 1 litre of water and extracted with 100 ml of toluene. The aqueous phase is basified to pH 8.5 with ammonium carbonate and then extracted twice with 500 ml of MTBE (methyl tert-butyl ether). The organic phase is dried over Na2S04, filtered, evaporated to dryness and then dried under vacuum over P205. 27 g (78% yield) of compound (a) are obtained in the form of a yellow liquid. (0211) The NMR and mass analyses are in accordance with the expected structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-86-7, 2-Methyl-1-phenyl-2-propanol, and friends who are interested can also refer to it.

Reference:
Patent; L’OREAL; SABELLE, Stephane; FADLI, Aziz; CHARRIER, Alexandra; (47 pag.)WO2017/109185; (2017); A1;,
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Reference of 15833-00-8 , The common heterocyclic compound, 15833-00-8, name is 2-(2-Aminophenyl)propan-2-ol, molecular formula is C9H13NO, 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.

112 g (1.13 mol) phosgene are piped into 500 mL THF. Then a solution of 52 g (0.34 mol) 2-(2-amino-phenyl)-propan-2-ol, prepared from 2-aminoacetophenone and methylmagnesium iodide, in 300 mL THF is added. The reaction mixture is left to stand overnight, concentrated by evaporation and combined with 500 ml of pyridine. After the pyridine has been distilled off the remainder is combined with water and extracted with diethyl ether. The organic phases are washed successively with 2 N hydrochloric acid, sodium hydroxide solution and water, dried with sodium sulphate and concentrated by evaporation. The residue remaining (46 g) is further reacted directly, without any more purification. M.p. (toluene/petroleum ether)=109-110 C.

The synthetic route of 15833-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2007/37781; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6971-51-3, (3-Methoxyphenyl)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, Product Details of 6971-51-3, blongs to alcohols-buliding-blocks compound. Product Details of 6971-51-3

A. m-Methoxybenzyl chloride To an ice cooled well stirred solution of 50 g. of m-methoxybenzyl alcohol in 500 ml. of benzene there are added, over the period of 20 minutes, 29 ml. of thionyl chloride in 40 ml. of benzene. At the end of an additional 30 minutes the ice bath was removed and the solution allowed to stand for 2 hours. Following this, the mixture was heated at reflux until the evolution of gas has ceased (30 minutes). The solvent was then removed in vacuum and the product distilled at 1.5 mm. There was obtained 39.94 g. of m-methoxybenzyl chloride, b.p. 63-69 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6971-51-3, (3-Methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; The Upjohn Company; US3947520; (1976); A;,
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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. 3973-18-0, name is Propynol ethoxylate, molecular formula is C5H8O2, 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. Quality Control of Propynol ethoxylate

General procedure: 4-hydroxy-2-butanone (20, 1.00 g, 11.35 mmol) was pipetted into a dry flask and cooled to 0C under nitrogen atmosphere. 7N methanolic ammonia (11.2 mL, 79 mmol) was added via syringe, and the solution was allowed to stir at 0C for 3 hours. A solution of hydroxylamine-O-sulfonic acid (1.476 g, 13.05 mmol) in methanol (9.7 mL) was added dropwise, then was allowed to stir for an additional 16 hours while slowly warming to room temperature. The reaction was filtered through a sintered glass funnel, then transferred to a reaction vessel and re-cooled to 0C. Triethylamine (1.58 mL,11.35 mmol) was added, then molecular iodine (2.88 g, 11.35 mmol) was added slowly in 10 equal portions until the purple/brown color of iodine persisted in the reaction vessel. The solvent was removed under reduced pressure, and purification of the crude isolate via Kugelrohr distillation (60C, 1-3 torr) delivered the 2,2-diazirinyl intermediate as a clear oil (304 mg, 27% yield). A portion of this intermediate (300 mg, 3.00 mmol) was dissolved in dry pyridine (6 mL) and cooled to 0C in an ice bath. To this solution was added p-toluenesulfonyl chloride (628 mg, 3.30 mmol). The reaction mixture was allowed to stir for 24 hours at 0-4C, then was poured into a mixture of 37%w/v HCl (15 mL) and ice (80 mL). The resulting suspension was extracted 3x with ether, then the pooled organic layers were washed with 1N HCl solution, 1N NaOH solution, water, and brine. The organic extract was dried over MgSO4, vacuum filtered, and concentrated to a clear oil (428 mg, 15% yield over 3 steps) used without further purification. TLC Rf (2:1 hex:EtOAc) = 0.6. 1HNMR (500 MHz, CDCl3) delta 7.82 (d, J = 7.9 Hz, 2H), 7.37 (d, J= 7.9 Hz, 2H), 3.96 (t, J = 6.4 Hz, 2H), 2.46 (s, 3H), 1.68 (t, J= 6.4 Hz, 2H), 1.01 (s, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 3973-18-0.

Reference:
Article; Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1538 – 1544;,
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Synthetic Route of 100-37-8, 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 100-37-8 as follows.

Preparation of diethylaminoethyl 5-(2,4-difluorophenyl) salicylate.AcOH [39] 11.7 g (0.1 mol) of diethylaminoethanol was dissolved in 10% sodium bicarbonate (200 ml) and acetone (100 ml). 31.1 g (0.1 mol) of 5-(2,4-difluorophenyl) acetylsalicyl chloride was added into the reaction mixture. The mixture is stirred for 3 hours at RT. The solvents are evaporated off. The residue is suspended in ethyl acetate (500ml). 5% sodium bicarbonate (200 ml) is added into the reaction mixture with stirring. Ethyl acetate layer is collected and washed with water ( 3 x 500 ml). The ethyl acetate solution was dried over anhydrous sodium sulfate. Sodium sulfate is removed by filtration. 6 g of acetic acid is added into the reaction mixture with stirring. The organic solution was evaporated off. After drying, it yielded 36 g of the desired product (88%). Hygroscopic product; Solubility in water: 400 mg/ml; Elementary analysis: C H F NO5; MW: 409.42. Calculated % C: 61.60; H: 6.15; F: 9.28; N: 3.42; O: 19.54; Found % C: 61.56; H: 6.18; F: 9.27; N: 3.40; O: 19.59. 1H-NMR (400 MHz, CDCl3): delta: 1.56 (t, 6H), 2.21 (s, 3H), 3.27 (m, 4H), 3.70(m, 2H), 4.69 (t, 2H), 4.9 (b, IH), 6.74 (m, IH), 6.84 (m, IH), 7.0 (b, H), 7.06 (b, IH), 7.15 (m, IH), 7.44 (m, IH), 7.86 (m, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100-37-8, its application will become more common.

Reference:
Patent; TECHFIELDS BIOCHEM CO. LTD; YU, Chongxi; WO2008/12603; (2008); A1;,
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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. 25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C9H11BrO

To a 0 C. mixture of 26A (7 g, 32.5 mmol) and NaHCO3 (3.28 g, 39.1 mmol) in DCM (200 mL) was added Dess-Martin periodinane (16.56 g, 39.1 mmol) and the reaction was allowed to slowly warm to rt overnight. The reaction was diluted with sat. aq. NaHCO3 (150 mL) and extracted with DCM (50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed (SiO2; 80 g; A=Hex, B=EtOAc; 20 min gradient from 0% B to 40% B; flow rate=60 mL/min) to afford the title compound (4.06 g, 19.1 mmol, 58.5% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) delta 9.82 (t, J=1.2 Hz, 1H), 7.48-7.37 (m, 2H), 7.19-6.97 (m, 2H), 3.02-2.88 (m, 2H), 2.83-2.70 (m, 2H).

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, 25574-11-2, 3-(4-Bromophenyl)propan-1-ol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Shi, Yan; Cheng, Peter T.W.; Wang, Ying; Jusuf, Sutjano; Tao, Shiwei; Zhang, Hao; Wu, Shung C.; Robl, Jeffrey A.; (87 pag.)US2017/253554; (2017); A1;,
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