Author: tianli

Application of 41175-50-2 ,Some common heterocyclic compound, 41175-50-2, 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.

To 10 mL DMF at 0oC was added dropwise POCl3 (1.73 mL, 18.5 mmol). The solution was stirred at 0oC for 15 min and then a solution of 3 (3.190 g, 16.9 mmol) in 11 mL DMF was added. The reaction was allowed to be stirred overnight at 0oC to rt. After that the reaction mixture was stirred at 0oC for 0.5 h and quenched by 10 mL water. After stirring for 15 min at rt, the reaction mixture was extracted with EtOAc and washed with water. The organic phase was dried over MgSO4 and evaporated under reduced pressure. The afforded syrup was subjected to flash chromatography purification (hexanes:EtOAc:CHCl3, 6:1:1) to give the product as a purple solid (3.080 g, yield: 84%). 1H NMR (400 MHz, CDCl3) d 11.79 (s, 1 H), 9.35 (s, 1 H), 6.82 (s, 1 H), 3.25 (m, 4 H), 2.66 (m, 4 H), 1.91 (m, 4 H).

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. 41175-50-2, 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Songbai; Wang, Wu-Hong; Dang, Ya-Li; Fu, Yuanqing; Sang, Ruocheng; Tetrahedron Letters; vol. 53; 32; (2012); p. 4235 – 4239;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 4461-39-6, 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. 4461-39-6, name is N-(2-Hydroxyethyl)-1,3-propanediamine. A new synthetic method of this compound is introduced below.

To a solution of 5-[[4-chloro-2-formyl-5-[[3-[3-[3-(4-hydroxy-l-piperidyl)propoxy]-2- methyl-phenyl]-2-methyl-phenyl]methoxy]phenoxy]methyl]pyridine-3-carbonitrile (300 mg, 468.63 pmol) in DMA (2 mL) was added 2-(3-aminopropylamino)ethanol (110.76 mg, 937.26 pmol), K2CO3 (80.96 mg, 585.79 pmol) and I2(356.83 mg, 1.41 mmol) at 0 C and the mixture was stirred at 0 C for 1 hr. The mixture was stirred at 25 C for 4 hr. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC (column: Luna Cl 8 100*30 5p; mobile phase: [water(0.05%HCl)-ACN] ;B%: l5%-45%, lOmin). The residue was purified by prep-HPLC (column: Waters Xbridge Prep OBD Cl 8 150*30 10m; mobile phase: [water(l0mM NH4HC03)-ACN]; B%: 20%-45%, lOmin). 5-[[4- chloro-2-[l -(2-hydroxy ethyl)-5,6-dihy dro-4H-pyrimi din-2-yl]-5-[[3-[3-[3-(4-hy droxy-l- piperidyl)propoxy]-2-methyl-phenyl]-2-methyl-phenyl]methoxy]phenoxy]methyl]pyridine-3- carbonitrile (16.21 mg, 4.50% yield) was obtained as a yellow solid. MS: m/z found 738.3[M+H]+; 1H NMR (400 MHz, DMSO-d6): d 9.01 (s, 1 H), 8.91 (s, 1 H), 8.31 (s, 1 H), 7.52-7.51 (m, 1 H), 7.30-7.16 (m, 4 H), 7.09-7.07 (m, 1 H), 6.97-6.94 (m, 1 H), 6.69-6.67 (m, 1 H), 5.35- 5.30 (m, 4 H), 4.53 (m, 2 H), 4.04-4.02 (m, 2 H), 3.33 (m, 2 H), 3.05 (m, 1 H), 2.67 (m, 4 H), 2.44-2.33 (m, 5 H), 2.04-1.82 (m, 12 H), 1.71-1.68 (m, 3 H), 1.40-1.35 (m, 2 H); 1H NMR (400 MHz, CD3OD): d 8.91-8.89 (m, 2 H), 8.26 (s, 1 H), 7.47-7.42 (m, 2 H), 7.26-7.08 (m, 4 H), 6.93- 6.91 (m, 1 H), 6.69-6.62 (m, 1 H), 5.39-5.32 (m, 4 H), 4.12-4.07 (m, 2 H), 3.62-3.30 (m, 7 H), 3.18-3.14 (m, 1 H), 2.85 (m, 2 H), 2.62-2.58 (m, 2 H), 2.21-1.87 (m, 15 H), 1.62-1.55 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4461-39-6, its application will become more common.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; BI, Yingzhi; DORSEY, Bruce D.; FAN, Yi; MOORE, Christopher Brooks; NGUYEN, Duyan; (169 pag.)WO2019/191624; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 10602-04-7, (4-Ethynylphenyl)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, Safety of (4-Ethynylphenyl)methanol, blongs to alcohols-buliding-blocks compound. Safety of (4-Ethynylphenyl)methanol

(4-((4-isopropoxy-3-methylphenyl)ethynyl)phenyl)methanolA solution of (4-ethynylphenyl)methanol (CAS 10602-04-7) (250 mgs, 1.9 mmol) in THF was treated with copper (I) iodide (7.2 mgs, 0.04 mmol) and then purged with Argon for 5 minutes. 4-iodo-1-isopropoxy-2-methylbenzene (CAS 877603-52-6) (579 mgs, 2.0 mmol), was then added followed by dichlorobis-(triphenylphosphine) palladium(II) (13.4 mgs, 0.019 mmol).The resultant mixture was heated at 80° C. overnight.The reaction mixture was filtered and the filtrate was evaporated to give the crude product.The crude product was purified on a column (MPLC) using hexane:ethyl acetate and gave Intermediate 4 (450 mgs, 76percent yield).1H-NMR (CDCl3, 300 MHz) delta=7.62 (s, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 7.18-7.24 (m, 1H), 6.840 (d, J=9.6 Hz, 1H), 5.39 (s, 2H), 4.54-4.60 (m, 1H), 2.12 (s, 3H), 1.31 (s, 3H), 1.27 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10602-04-7, (4-Ethynylphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; US2012/129906; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 627-27-0, 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. 627-27-0, name is But-3-en-1-ol. A new synthetic method of this compound is introduced below.

In a 1000 ml rb flask were placed 3-buten-1-ol (7.21 g, 100.00 mmol), 3,4-dihydro-2H-pyran (12.62 g, 150.00 mmol) and pyridinium p-toluenesulfonate (2.51 g, 10.00 mmol) in 350 ml of anhydrous dichloromethane. The reaction mixture was stirred at room temperature for 4 h. Then the reaction mixture was concentrated and the residue was purified by column with Hexane/Ethyl acetate=100/5 to provide 13.90 g of the desired product as an oil (89.0%). 1H-NMR (DMSO-d6) delta 5.851-5.742 (m, 1H), 5.103-5.011 (d, 1H), 4.997-4.985 (d, 1H), 4.555-4.537 (t, 1H), 3.745-3.611 (m, 2H), 3.433-3.347 (m, 2H), 2.290-2.236 (m, 2H), 1.698-1.675 (m, 2H), 1.611-1.566 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,627-27-0, its application will become more common.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/298297; (2010); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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.504-63-2, name is 1,3-Propanediol, molecular formula is C3H8O2, molecular weight is 76.0944, as common compound, the synthetic route is as follows.Application In Synthesis of 1,3-Propanediol

General procedure: To a solution of substrate (1 mmol) and acetic anhydride (1.5 mmol) was added supported iron catalyst (Fe/SBA-15) (0.005 mmol, 0.085 g) and the mixture was stirred at 40 C. After completion of the reaction (TLC), the reaction mixture was filtered and the catalyst rinsed with ethyl acetate and heated at 70 C prior to its reuse in the next reaction. The organic layer was washed with saturated NaHCO3 and water, and dried over anhydrous sodium sulfate. The product was obtained after removal of the solvent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,504-63-2, 1,3-Propanediol, and friends who are interested can also refer to it.

Reference:
Article; Rajabi, Fatemeh; Luque, Rafael; Catalysis Communications; vol. 45; (2014); p. 129 – 132;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts