Category: alcohols-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 32328-03-3, Diethyl 3-hydroxyglutarate, 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, Application In Synthesis of Diethyl 3-hydroxyglutarate, blongs to alcohols-buliding-blocks compound. Application In Synthesis of Diethyl 3-hydroxyglutarate

General Preparation of 3-hvdroxy protected glutaric acid. A four-neck round bottom flask fitted with a mechanical stirrer, condenser and charging tube, was charged with methylene dichloride (675 ml) followed by charging of imidazole (187.2 g), t-butyldimethylsilyl chloride (248.3 g) under nitrogen atmosphere. Reaction mass was maintained for 1-2 hours at 20-300C followed by addition of a solution of 3-hydroxy diethyl glutarate in methylene chloride (225 g). The mass was maintained for 4-6 hours followed by water and brine washing of the reaction mass. Methylene dichloride under vacuum at 30- 350C was distilled out and residue was charged into a solution of 30-40% aq. methyl alcohol (1850 ml), sodium hydroxide (96.8 g) at 25-350C and mixed for 20-30 hours. Solvent is distilled out under vacuum at 40-450C, mass was further diluted with water and 1-12N hydrochloric acid was added to bring pH to 2.5-4 and the product was extracted with t-butyl methyl ether and concentrated to give 71 % of 3-hydroxy protected glutaric acid.

The synthetic route of 32328-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2008/130638; (2008); A2;,
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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.2854-16-2, name is 1-Amino-2-methylpropan-2-ol, molecular formula is C4H11NO, molecular weight is 89.14, as common compound, the synthetic route is as follows.Product Details of 2854-16-2

To a suspension of aminomalononitrile 7-toluenesulfonate (2.0 g, 7.9 mmol, 1.0 equiv) in THF (30 mL) at 25 °C was added NE.3 (1.3 mL, 9.5 mmol, 1.2 equiv) in one portion. The mixture was stirred for 30 min to afford a homogeneous solution. To this solution was added triethyl orthovalerate S3 (2.2 mL, 9.5 mmol, 1.2 equiv) and the solution was heated at reflux for 3 h. TLC indicated the presence of starting material, thus additional triethyl orthovalerate (1.1 mL, 4.7 mmol, 0.6 equiv) was added. The solution was heated at reflux for another 2 h then cooled to 25 °C. Next, NEt3 (1.3 mL, 9.5 mmol, 1.2 equiv) and l-amino-2-methylpropan-2-ol S2 (844 mg, 9.5 mmol, 1.2 equiv) were added sequentially and the reaction was stirred at 25 °C for 15 h. The reaction was concentrated in vacuo and the resulting solid residue was redissolved in CH2C12 (100 mL) and washed with saturated aqueous Na2C03 solution (25 mL). The aqueous layer was extracted with CH2C12 (3 x 20 mL). The combined organic fractions were washed with saturated aqueous NaCl, dried (MgS04) and concentrated in vacuo. Purification by flash column chromatography on silica gel (CH2Cl2-9/l MeOH/CH2Cl2, gradient) afforded the title compound (1.55 g, 83percent) as an off white solid: 1H NMR (CD3OD, 600 Hz) delta 0.94 (t, J- 6.0 Hz, 3H), 1.23 (s, 6H), 1.37 (hex, J- 7.8 Hz, 2H), 1.66 (pent, J= 6.0 Hz, 2H), 2.60 (t, J= 6.0 Hz, 2H), 3.79 (s, 2H); 13C NMR (CD3OD, 150 Hz) delta 12.7, 21.9, 26.0, 26.4, 29.1, 52.9, 71.2, 89.5, 116.2, 145.2, 149.2; MS (ESI+): calcd C12H21N40 [M + H]+ 237.3, found 237.4.

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; REGENTS OF THE UNIVERSITY OF MINNESOTA; FERGUSON, David M.; OHLFEST, John; ALDRICH, Courtney; WO2013/33345; (2013); A1;,
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Synthetic Route of 136-80-1, 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. 136-80-1, name is N-(2-Hydroxyethyl)-2-methylaniline, molecular formula is C9H13NO, 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.

This embodiment provides a quinone compound, and its reaction formula is:In a reaction flask, 5 mmol of N-hydroxyethyl-2-methylaniline and 7.5 mmol of 2-methylaniline provided in Example 2 were weighed out and dissolved in 200 ml of acetonitrile, and Sn/activated carbon loaded catalyst was added, and TLC was used to detect N. The reaction was stopped after the reaction of hydroxyethyl-2-methylaniline was completed.After isolation and purification, 7-methylindole was obtained (yield 64.3%).

According to the analysis of related databases, 136-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chongqing Huage Biochemical Co., Ltd.; He Xiaoqiang; Chen Zhizhong; Wu Chengli; (8 pag.)CN107445881; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 4415-82-1, Cyclobutylmethanol, 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, 4415-82-1, blongs to alcohols-buliding-blocks compound. Formula: C5H10O

A solution of cyclobutanemethanol (4.0 g, 46.4 mmol) in dichloromethane (28 mL) at 25 C. was treated with 4-dimethylaminopyridine (6.23 g, 50.9 mmol). The reaction was then cooled to 0 C. and was treated with para-toluenesulfonylchloride (8.95 g, 46.94 mmol). The reaction was allowed to slowly warm to 25 C. and was allowed to stir overnight. After this time, the reaction was partitioned between water (200 mL) and methylene chloride (2×200 mL). The combined organics were washed with a 1N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution (1×200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford toluene-4-sulfonic acid cyclobutylmethyl ester (10.87 g, 97%) as colorless oil which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4415-82-1, its application will become more common.

Reference:
Patent; Berthel, Steven Joseph; Haynes, Nancy-Ellen; Kester, Robert Francis; McDermott, Lee Apostle; Qian, Yimin; Sarabu, Ramakanth; Scott, Nathan Robert; Tilley, Jefferson Wright; US2009/264434; (2009); 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. 100-37-8, name is 2-(Diethylamino)ethanol. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Diethylamino)ethanol

165 g of ibuprofen and 160 mL of isopropyl acetate were placed in a pre-dried 500 mL three-necked flask and equipped with a reflux and agitation device; 64 mL of thionyl chloride was slowly added to the three-necked flask with stirring, and the mixture was stirred at room temperature for 30 minutes and then heated to reflux. Keep refluxed for 2-3 hours; The reaction mixture was rotary evaporated until No fraction dropout, and evaporated to dryness by adding 120 mL of n-hexane, and 120 mL of isopropyl acetate was added thereto, and the distillation was continued until no fraction was dropped, and the distillation was repeated once with isopropyl acetate. The evaporated mixture was dissolved in 600 mL of isopropyl acetate and transferred to a pre-dried 2 L three-necked flask, stirred and cooled to below 10 C; 93.6g of 2-(diethylamino)ethanol was slowly added dropwise to the above three necked flask through a constant pressure dropping funnel, and the temperature was controlled within 10 C, after the completion of the dropwise addition, stirring was continued at 0-10 C for 0.5 hours; 88 g of anhydrous potassium carbonate solid was added to the above three-necked bottle in portions, stirred at 5-10 C for 30 minutes, then slowly warmed to 15-25 C, and stirred at this temperature for 8-10 hours; 320 mL of deionized water was added to the above reaction solution, stirred for 15-30 minutes, and the organic phase was separated. The organic phase was washed four times with deionized water (320 mL X 4) and dried over anhydrous sodium sulfate. Filtration, then washed solid sodium sulfate with a small amount of isopropyl acetate; The above organic phase was transferred to a 2L three-necked flask, and the temperature was lowered to below 10 C, and about 32 g of hydrogen chloride gas was introduced at 0-10 C and maintained it for 1- 2 hours, then Concentrated a part of the solution, added 120 mL of n-hexane under stirring, added 1 g of seed crystals, and sealed and placed in refrigerator for crystallization; Filtration, washing with ethyl acetate / n-hexane (V / V = 1:1, 200 ml X 2); The obtained solid was dried under vacuum at 40-50 C until the water (moisture content )is qualified, to obtain 178.56 g of a crystalline crystal, a molar yield of 65.2%, and a purity of 99.76 %.

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

Reference:
Patent; Tianjin Xinchen Taifeier Pharmaceutical Technology Co., Ltd.; Yao Chen; (25 pag.)CN108727206; (2018); A;,
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Related Products of 5182-44-5 ,Some common heterocyclic compound, 5182-44-5, molecular formula is C8H9ClO, 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-(3-chlorophenyl)acetaldehyde[115] The mixture of Example 86A (5.73 g, 36.5 mmol) and Dess-Martin periodinane (18.6 g, 43.8 mmol) in 200 mL of dichloromethane was stirred under 2 atmosphere for 4 hours at room temperature. Then saturated aHC03 (500 mL) and a2S2C>3 (100 mL) was added with stirring for another 30 minutes. The mixture was extracted with dichloromethane (3 x 300 mL). The organic layers were combined, dried over Na2S04, filtered, and concentrated. The crude product was purified by distillation under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5182-44-5, its application will become more common.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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Reference of 627-30-5 ,Some common heterocyclic compound, 627-30-5, molecular formula is C3H7ClO, 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.

The 4-CHLORO-7- (3-CHLOROPROPOXY)-6-METHOXYQUINAZOLINE used as a starting material was prepared as follows:- Ammonium formate (45 g) was added portionwise over 1.25 hours to a stirred mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (International Patent Application WO 02/16352, Example 1 thereof; 20 g), 10% palladium-on-carbon catalyst (3.3 g) and DMF (530 ml) and the reaction mixture was stirred for an additional 30 minutes. The catalyst was removed by filtration and the solvent was evaporated. There was thus obtained 7-hydroxy- 6-methoxy-3,4-dihydroquinazolin-4-one (8.65 g); NMR Spectrum: (DMSOD6) 3.9 (s, 3H), 7.0 (s, 1H), 7.45 (s, 1H), 7.9 (s, 1H). A mixture of the material so obtained, acetic anhydride (63 ml) and pyridine (7.5 ml) was heated to 100C for 4.5 hours. The resultant mixture was allowed to stand at ambient temperature for 16 hours. The mixture was poured into a stirred mixture (400 ml) of ice and water. The resultant precipitate was isolated and dried under vacuum. Analysis revealed that hydrolysis of the acetate group on the 4 position of the quinazoline was incomplete. The mixture was therefore further hydrolysed with water (150 ml) and pyridine (a few drops) at 90C for 15 minutes. The resultant mixture was cooled to ambient temperature and the solid was collected by filtration, washed with water and dried under vacuum. There was thus obtained 7-ACETOXY-6-METHOXY-3, 4-dihydroquinazolin-4-one (7.4 g); NMR Spectrum: (DMSOD6) 2.3 (s, 3H), 3.9 (s, 3H), 7.45 (s, 1IN), 7.65 (s, 1H), 8. 05 (s, 1H). A mixture of A portion (2 g) of the material so obtained, thionyl chloride (32 ml) and DMF (5 drops) was stirred and heated to reflux for 1.5 hours. The mixture was cooled to ambient temperature and the excess of thionyl chloride was evaporated. Toluene was added to the residue and evaporated. The resultant residue was diluted with methylene chloride (15 ml) and a 10% ammonia solution in methanol (80 ml) was added and the mixture was heated to 80C for 10 minutes. The mixture was cooled to ambient temperature and evaporated. Water was added to the residue and the mixture was neutralised by the addition of dilute aqueous hydrochloric acid solution. The resultant precipitate was collected by filtration and dried under vacuum at 35C for 16 hours. There was thus obtained 4-chloro- 7-hydroxy-6-methoxyquinazoline (1.65 g); NMR Spectrum: (DMSOD6) 4.0 (s, 3H), 7.25 (s, 1H), 7.4 (s, 1H), 8.8 (s, 1H). Di-tert-butyl azodicarboxylate (2.3 g) was added portionwise over a few minutes to a stirred mixture of 4-chloro-7-hydroxy-6-methoxyquinazoline (1.65 g), 3-chloropropanol (0.7 ml), triphenylphosphine (2.6 g) and methylene chloride (100 ml) and the reaction mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated to a volume of about 30 ml by evaporation and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b. p 40-60C) and ethyl acetate as eluent. There was thus obtained 4-CHLORO-7- (3-CHLOROPROPOXY)-6-METHOXYQUINAZOLINE as a white solid (2 g); NMR Spectrum: (DMSOD6) 2.3 (m, 2H), 3. 8 (m, 2H), 4.05 (s, 3H), 4.4 (m, 2H), 7.45 (s, 1H), 7.55 (s, 1H), 8.9 (s, 1H).

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. 627-30-5, 3-Chloropropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/81000; (2004); A1;,
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Related Products of 1875-88-3 ,Some common heterocyclic compound, 1875-88-3, molecular formula is C8H9ClO, 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.

(9A) Ethyl 3-{4-[2-(4-chlorophenyl)ethoxy]phenyl}-3-ethoxypropionate Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 2-(4-chlorophenyl)ethanol (99 mg, 0.630 mmol) were dissolved in tetrahydrofuran (10 mL), and triphenylphosphine (178 mg, 0.680 mmol) and a 40percent diethyl azodicarboxylate toluene solution (309 muL, 0.680 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 4 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a yellow oily substance (151 mg, yield: 95percent). 1H NMR (CDCl3, 400 MHz): delta1.13 (3H, t, J=7.0 Hz), 1.23 (3H, t, J=7.0 Hz), 2.55 (1H, dd, J=5.0, 15.2 Hz), 2.79 (1H, dd, J=9.0, 15.2 Hz), 3.06 (2H, t, J=7.0 Hz), 3.30-3.38 (2H, m), 4.14 (4H, t, J=7.3 Hz), 4.68 (1H, dd, J=5.0, 8.9 Hz), 6.86 (2H, d, J=8.6 Hz), 7.22 (2H, d, J=8.3 Hz), 7.24 (2H, d, J=8.6 Hz), 7.28 (2H, d, J=8.6 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1875-88-3, its application will become more common.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; US2011/53974; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3344-77-2, 12-Bromododecan-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, COA of Formula: C12H25BrO, blongs to alcohols-buliding-blocks compound. COA of Formula: C12H25BrO

vi) Cholesteryl 12-hydroxydodecylcarbamate from cholesteryl chloroformate and 12-aminododecan-1-ol. 12-Aminododecanl-1-ol is prepared from 12-bromododecan-1-ol and sodium azide in refluxing 95% ethanol, followed by catalytic hydrogenation (10% Pd/C catalyst, 30 psi hydrogen) in methanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3344-77-2, 12-Bromododecan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Dharmacon, Inc.; US2008/85869; (2008); A1;,
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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. 7287-81-2, name is 1-(m-Tolyl)ethanol, molecular formula is C9H12O, 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. Computed Properties of C9H12O

General procedure: Firstly, GO (0.01 g) was added into water (3 mL) and the mixturecould generate the stable colloidal suspensions under a mild ultrasonictreatment. Afterwards, the alcohol (2 mmol) and (NH4)5H5[H2(WO4)6](0.03 mmol, M=1602) were added. The mixture was stirred for 15 min atroom temperature. Subsequently, hydrogen peroxide (30 wt%, 8 mmol)was added dropwise and the mixture was heated to 70C until thereaction was fully completed (monitored by TLC). After the reactioncompleted, GO could be readily separated from the mixtures bycentrifugation, and then ethyl acetate was added to the mixture to extract organic constituents. Finally, the organic extracts were concentratedunder reduced pressure and purified by column chromatography.

With the rapid development of chemical substances, we look forward to future research findings about 7287-81-2.

Reference:
Article; Fu, Huihui; Hu, Chuanfeng; Huang, Zhida; Zhou, Jianhao; Peng, Xinhua; Synlett; vol. 29; 4; (2018); p. 447 – 451;,
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