Category: alcohols-buliding-blocks

Synthetic Route of 78573-45-2, 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 78573-45-2 as follows.

(e) p-Toluenesulfonic acid [3-(3-trifluoromethylphenyl)propyl] ester 125 g of p-toluenesulfonic acid [3-(3-trifluoromethylphenyl)propyl] ester are obtained as a yellow oil from 71.5 g of 3-(3-trifluoromethylphenyl)propan-1-ol, 83 g of p-toluenesulfonic acid chloride and 54 ml of pyridine in 160 ml of chloroform by the procedure described in Example 5e.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78573-45-2, its application will become more common.

Reference:
Patent; BYK Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4324796; (1982); A;,
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Application of 179811-63-3, 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. 179811-63-3, name is 2-Amino-2-(3-chlorophenyl)ethanol, molecular formula is C8H10ClNO, 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 20 (2.60 mmol) and corresponding amine (2.60 mmol) in MeOH (10 mL) was added Et3N (540.00 mul, 3.90 mmol). The mixture was refluxed for 6h. After completion, the mixture was cooled to 0 oC, and stirred for 30 min, the precipitate was filtered to obtain corresponding product. 2.16.1. 2-(1-(3-chlorophenyl)-2-hydroxyethyl)-6-(2-(methylsulfonyl) pyrimidin-4-yl) isoi-ndolin-1-one (21a) Yield 65%. m.p. 166~167 oC. 1H NMR (300 MHz, CDCl3) delta (ppm): 9.01 (d, J = 5.30 Hz, 1H, ArH), 8.49 (s, 1H, ArH), 8.44 (dd, J = 8.00, 1.50 Hz, 1H, ArH), 8.01 (d, J = 5.30 Hz, 1H, ArH), 7.58 (d, J = 8.00 Hz, 1H, ArH), 7.50-7.31 (m, 3H, ArH), 7.28-7.26 (m, 1H, ArH), 5.40 (dd, J = 7.90, 4.40 Hz, 1H, CHCH2OH), 4.63 (d, J = 17.80 Hz, 1H, CH2), 4.43 – 4.32 (m, 2H, HOCH2CH), 4.28 (dd, J = 11.90, 4.40 Hz, 1H, CH2), 3.49 (s, 3H, SO2CH3 ).

According to the analysis of related databases, 179811-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ji, Dezhong; Zhang, Lingzhi; Zhu, Qihua; Bai, Ying; Wu, Yaoyao; Xu, Yungen; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 334 – 341;,
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Electric Literature of 14320-38-8, 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 14320-38-8, name is Cyclopent-3-enol. This compound has unique chemical properties. The synthetic route is as follows.

Cyclopent-3-enol (2.1 g, 24.97 mmol) was dissolved in CH2CI2 (30 ml,). TIPS-Cl (10.58 mL, 49.9 mmol) was added, followed by imidazole (3.40 g, 49.9 mmol). The mixture was stirred at room temperature for 2 days. White solid was filtered out and washed with small amount of DCM. The organic solution was evaporated and the residue was purified by silica gel chromatography (80 g silica gel column, 0-50% EtOAc/hexane gradient). Removing solvent gave (cyclopent-3-en-l -y]oxy)triisopropylsilane (4.92 g, 20.46 mmol, 82 % yield) as a colorless oil. NMR (400 MHz, CDCb): delta ppm 5.67 (2 H, s), 4.63 (1 H, t, ./ 3.63 Hz), 2.62 (2 H, dd, ./ 14.97. 6.82 Hz), 2.20 – 2.45 (2 H, m), 1.00 – 1.13 (21 H, m).

According to the analysis of related databases, 14320-38-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FU, Qinghong; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (184 pag.)WO2018/13770; (2018); A1;,
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Reference of 50411-26-2, Adding some certain compound to certain chemical reactions, such as: 50411-26-2, name is 1-Amino-3-phenylpropan-2-ol,molecular formula is C9H13NO, 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 50411-26-2.

To a stirring solution of 1-amino-3-phenyl-propan-2-ol (0.51 g, 3.3 mmol) and triethylamine (0.45 mL, 3.3 mmol) in 20 mL dichloromethane was added (0.92 g, 2.6 mmol) 2-chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one. The solution was stirred for 18 h at room temperature. The solution was diluted with ethyl acetate and washed with 5% sodium bicarbonate. The organic layer was dried over magnesium sulfate and purified on 10 g silica eluting product with 0 to 5% methanol/dichloromethane to give a pale yellow solid. M+1=463.2.

According to the analysis of related databases, 50411-26-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; US2005/43301; (2005); A1;,
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Application of 928-51-8 ,Some common heterocyclic compound, 928-51-8, molecular formula is C4H9ClO, 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.

NaI (450 mg, 3.00 mmol) and anhydrous NaHCO3 (1.512 g, 24.0 mmol) were added to a solution of the amine Int-m2 (1.468 g, 6.00 mmol) and 4-chlorobutan-l-ol (1.299 g, 12.0 mmol) in dry acetonitrile (12 mL). After being stirred overnight at 900C for 18 h. The mixture was cooled to RT, and diluted with EA, washed with water and brine. The organic phase was dried (Na2SO4), filtered and concentrated. Purified by flash chromatograpy give a yellowish oil Int-n2 (1.104 g, 58%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,928-51-8, its application will become more common.

Reference:
Patent; LIU, Jun, O.; HU, Xiaoyi; CHEN, Xiaochun; MA, Dawei; BHAT, Shridhar; WO2009/64388; (2009); A2;,
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Electric Literature of 1805-32-9, 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 1805-32-9, name is 3,4-Dichlorobenzyl alcohol. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 3,4-dichlorobenzyl alcohol (0.21 g, 1.20 mmol) in DMSO (5 mL) was added potassium rt-butoxide (0.29 g, 2.58 mmol). The mixture was stirred at ambient temperature for 5 minutes and 5-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide (Preparation 3) (0.30 g, 1.01 mmol) was added. After 0.5 h, the reaction mixture was diluted with ethyl acetate (150 mL), washed with IN hydrochloric acid (2 chi 150 mL), brine (150 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to provide a residue which was purified by HPLC using Method A. The title compound was obtained as a white solid (0.03 g, 7%): NMR (300 MHz, DMSO-de) 6 11.78 (s, 1H), 7.75-7.66 (m, 3H), 7.43 (d, J= 8.2 Hz, 1H), 7.31 (d, J= 12.1 Hz, 1H), 5.28 (s, 2H), 2.83 (s, 6H); MS (ES-) m/z 453.0, 455.0 (M – 1).

According to the analysis of related databases, 1805-32-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; DEHNHARDT, Christoph Martin; CHOWDHURY, Sultan; FOCKEN, Thilo; GRIMWOOD, Michael Edward; HEMEON, Ivan William; SAFINA, Brian; SUTHERLIN, Daniel, P.; WO2014/8458; (2014); A2;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 111-46-6, name is 2,2′-Oxybis(ethan-1-ol), the common compound, a new synthetic route is introduced below. Formula: C4H10O3

General procedure: Preparation of 2-(2-(trityloxyl)ethoxyl)ethanol 3a is used as an example. To a stirring solution ofdiethylene glycol 2a (34.4 g, 324.0 mmol), DMAP (1.3 g, 10.8 mmol) and triethylamine (18.7 mL,130.0 mmol) in CH2Cl2 (200 mL) at 40oC was slowly added a solution of triphenylmethyl chloride(30.1 g, 108.0 mmol) in CH2Cl2 (100 mL) over an hour. After the addition, the mixture was refluxed until no more triphenylmethyl chloride can be detected by TLC (usually 2-3h). Then, the mixture was cooled and poured into brine (300 mL), extracted with CH2Cl2 (150 mL, three times). The combined organic phase was dried over anhydrous Na2SO4, concentrated under vacuum, purified by flash chromatography on silica gel to give 3a as white wax (30.7 g, yield: 82%). 1H NMR (400MHz, CDCl3) delta 3.27 (t, J = 6.0 Hz, 2H), 3.61 (t, J = 4.0 Hz, 2H), 3.66-3.73 (m, 4H), 7.20-7.31 (m,9H), 7.45-7.47 (m, 6H).

The synthetic route of 111-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yu; Thapa, Bijaya; Zhang, Hua; Li, Xuefei; Yu, Fanghua; Jeong, Eun-Kee; Yang, Zhigang; Jiang, Zhong-Xing; Tetrahedron; vol. 69; 46; (2013); p. 9586 – 9590;,
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Related Products of 68327-04-8 ,Some common heterocyclic compound, 68327-04-8, molecular formula is C5H12ClNO, 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 65 mg intermediate 6-[4-(d ifluoromethyl )phenyl]-3-oxo-2-(pyrid in-3-yl)-2,3-dihydropyridazine-4-carboxylic acid, 60 mg (1 S,2S)-2-aminocyclopentanol hydrochloride (1:1),144 mg HATU, 0.1 mL ethyldiisopropylamine and 1 mg 4-dimethylaminopyridine in 2 mL ofDMF was stirred at room temperature for 14 hours. Then the reaction mixture was filtered andsubjected to RP-HPLC (instrument: Labomatic HD-3000 HPLC gradient pump, LabomaticLabocol Vario-2000 fraction collector; column: Chromatorex 0-18 125 mm x 30 mm, eluent A:0.lvol% formic acid in water, eluent B: acetonitrile; gradient: A 85% B 15% – A 45%/B55%; flow: 150 mL/min; UV-detection: 254 nm) to yield 13 mg 6-[4-(difluoromethyl)phenyl]-N-[(1 S ,2S)-2-hyd roxycyclopentyl]-3-oxo-2-(pyridin-3-yl)-2 ,3-d ihyd ropyridazine-4-carboxamide.1H NMR (400 MHz, DMSO-d6) 6 [ppm] = 1.39-1.56 (m, 2 H), 1.58-1.76 (m, 2 H), 1.77-1.87(m, 1 H), 2.04 -2.14 (m, 1 H), 3.94 (br d, 1 H), 3.98-4.07 (m, 1 H), 4.95 (br d, 1 H), 7.13 (t, 1H), 7.64 (dd, 1 H), 7.72 (d, 2 H), 8.13 (d, 2 H), 8.15-8.20 (m, 1 H), 8.66-8.72 (m, 2 H), 8.92(d, 1 H), 9.31 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,68327-04-8, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM; GUTCHER, Ilona; ROeHN, Ulrike; SCHMEES, Norbert; ZORN, Ludwig; ROeSE, Lars; BADER, Benjamin; KOBER, Christina; CARRETERO, Rafael; STOeCKIGT, Detlef; IRLBACHER, Horst; PLATTEN, Michael; (397 pag.)WO2018/146010; (2018); 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. 145691-59-4, name is (3,5-Dibromophenyl)methanol, molecular formula is C7H6Br2O, 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. name: (3,5-Dibromophenyl)methanol

1,3-Dibromo-benzyl alcohol (1) (20 g, 75.2 mmol) was dissolved in anhydrous DCM (200 mL) in a dried flask under nitrogen. The reaction mixture was cooled to 0 ¡ãC and stirred under nitrogen atmosphere. DIPEA (25.8 mL, 150.4 mmol) was added drop wise to the above solution, after 10 minutes of stirring at 0 ¡ãC, mesyl cholride (8.7 mL, 112.8 mmol) was added drop-wise to the above reaction mixture. Finally, the reaction mixture was allowed to stir at RT for 2 hrs. Reaction mixture was diluted with DCM, washed with water (100 mL) followed by NaHC03 solution and brine, dried over anhydrous Na2S04, filtered and evaporated to dryness to give 21 gm of crude product (2) as a brown liquid which was carried forward to the next step as such.

With the rapid development of chemical substances, we look forward to future research findings about 145691-59-4.

Reference:
Patent; SAINT LOUIS UNIVERSITY; RUMINSKI, Peter; GRIGGS, David; WO2014/15054; (2014); 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.307353-32-8, name is Methyl 3-bromo-5-(hydroxymethyl)benzoate, molecular formula is C9H9BrO3, molecular weight is 245.07, as common compound, the synthetic route is as follows.Product Details of 307353-32-8

In a three-necked flask with a capacity of 3 liters, 253.11g of methyl 5-bromo-3-(hydroxymethyl)benzoate were placed and mixed with 2000 ml of toluene, and the resultant mixture was agitated to prepare a solution. The resultant solution was mixed with 44g of manganese dioxide, and the resultant reaction mixture liquid was heated to a temperature of 105C and agitated for 7 hours. The resultant reaction mixture liquid was allowed to be cooled to room temperature and filtered to remove a solid fraction therefrom, and the resultant filtrate was concentrated. The target compound, methyl 5-bromo-3-formylbenzoate was obtained in an amount of 236.79g which corresponded to a yield of 94.3%. The results of the 1H-NMR (200 MHz, delta ppm, CDCl3) of the resultant compound were as follows. 3.98 (s, 3H), 8.1 – 8.3 (m, 1H), 8.3 – 8.6 (m, 2H), 10.0 (s, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,307353-32-8, Methyl 3-bromo-5-(hydroxymethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; TEIJIN LIMITED; EP1460059; (2004); A1;,
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