Category: alcohols-buliding-blocks

Electric Literature of 456-47-3 ,Some common heterocyclic compound, 456-47-3, molecular formula is C7H7FO, 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.

General procedure: A mixture of H2O (5 mL) and CH2Cl2 (5 mL) wasadded to the chlorinated polymeric beads (2 g). (The unchlorinated beads were obtained from HaloSource, Inc. The unchlorinated beads were chlorinated by soaking the beads in bleach solution, with pH adjusted to 7 by additionof AcOH, for an hour. Then, the chlorinated beads were filtered and dried in air.) After addition of TEMPO (10 mg,0.064 mmol) and benzyl alcohol (0.2 g, 1.8 mmol), NaHCO3(0.5 g) was added to the mixture. The mixture was stirred at r.t. for 3 h and filtered. The residue on the filter paper was washed with H2O (20 mL) and CH2Cl2 (10 mL), and the organic phase of the filtrate was separated, dried over MgSO4, and filtered. The solvent was removed under vacuum to obtain benzaldehyde.

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. 456-47-3, 3-Fluorobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Akdag, Akin; Oeztuerk, Perihan; Synlett; vol. 24; 18; (2013); p. 2451 – 2453;,
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Synthetic Route of 349-75-7, 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.349-75-7, name is (3-(Trifluoromethyl)phenyl)methanol, molecular formula is C8H7F3O, molecular weight is 176.14, as common compound, the synthetic route is as follows.

Sequentially capturing meso-Co-N / C (800) (35mg, 0.25mol% Co), 3- trifluoromethyl-benzyl alcohol (176mg, 1mmol), a concentration of 28 mass% aqueous ammonia (280 L) was added to the reaction flask 10ml and tert-amyl alcohol was added 1ml of solvent placed in the reaction vessel, the oxygen charged to 1Mpa, placed in an oil bath of 130 and then detecting the extent of reaction by GC-MS.After completion of the reaction, the biphenyl internal standard was added, the product was analyzed 3-trifluoromethyl-benzonitrile quantitative yield by GC.The reaction 24h, 3- trifluoromethyl-benzonitrile in 83% yield, selectivity of 99%.

The chemical industry reduces the impact on the environment during synthesis 349-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dalian Institute of Chemical Physics; Gao Shuang; Shang Sensen; Wang Lianyue; Lv Ying; (7 pag.)CN106883143; (2017); 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.349-75-7, name is (3-(Trifluoromethyl)phenyl)methanol, molecular formula is C8H7F3O, molecular weight is 176.14, as common compound, the synthetic route is as follows.SDS of cas: 349-75-7

General procedure: 1-methyl-3-[(3-cyanophenylmethoxy)methyl]-2(1H)-pyridinone, 12a. To a 0 C suspension of sodium hydride (41 mg, 60% suspension in mineral oil, 1.01 mmol), in THF (3 mL) was added 3-cyanobenzyl alcohol (100 mg, 0.75 mmol). After the mixture was stirred for 1 h at 0 C, 3-(bromomethyl)-1-methylpyridin-2(1H)-one3 (152 mg, 0.75 mmol) in THF (3mL) was added dropwise. The reaction mixture was slowly allowed to warm to room temperature and stirred for additional 3 h before diluting with saturated aqueous ammonium chloride. After extraction with ethyl acetate, the combined organics were washed with brine, concentrated invacuo and purified by column chromatography using 5:95 MeOH/DCM to get title compound as a colorless soild (136 mg, 71 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,349-75-7, (3-(Trifluoromethyl)phenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Khatri, Buddha B.; Vrubliauskas, Darius; Sieburth, Scott McN.; Tetrahedron Letters; vol. 56; 30; (2015); p. 4520 – 4522;,
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Synthetic Route of 50595-15-8, 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 50595-15-8, name is tert-Butyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromo-3H-oxazolo[4,5-b]pyridin-2-one (300 mg, 1.4 mmol) in THF (5 mL) was added tert-butyl 2-hydroxyacetate (553.23 mg, 4.19 mmol), PPh3 (731.97 mg, 2.79 mmol) and then DIAD (564.31 mg, 2.79 mmol). The resulting mixture was stirred at 25 °C under N2 for 16 hours to give a solution. The reaction solution was concentrated to give a residue. Water (20 mL) was added to the residue, and the mixture was extracted with EtOAc (20 mL x 2). The combined organic layer was washed with brine (20 mL x 2), dried over anhydrous Na2SC>4, filtered and concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0percent to 10percent to 30percent) to give the product (400 mg, 1.22 mmol, 87percent yield) as a solid. *H NMR CDC13, 400MHz deltaH = 7.33 – 7.29 (m, 1H), 7.27 – 7.24 (m, 1H), 4.55 (s, 2H), 1.48 (s, 9H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 50595-15-8, tert-Butyl 2-hydroxyacetate.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
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Electric Literature of 20712-12-3, Adding some certain compound to certain chemical reactions, such as: 20712-12-3, name is (2-Amino-5-bromophenyl)methanol,molecular formula is C7H8BrNO, 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 20712-12-3.

(l) To a mixture of lithium aluminum hydride (2.6 g, 69 mmol) in diethyl ether (54 ml) was added dropwise 5-bromoanthranillic acid methyl ester (6.3 g, 27 mmol) in diethyl ether (54 ml) at Ot). The mixture was stirred at O1C for 3 hours. Then water (2.6 ml), 15 wtpercent aqueous solution of sodium hydroxide (2.6 ml) and water (7.8 ml) was addedsequentially at O1C. The mixture was filtrated through a pad of Celite, and concentrated in vacuo. The residue was dissolved into tetrahydrofuran (160 ml), and triethylamine (15 g, 150 mmol) was added. The mixture was cooled to Ot, and trichloromethyl chloroformate (2.9 g, 15 mmol) was added. The mixture was stirred at room temperature for 4 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford crude product. This crude product was washed with diethyl ether to afford6-bromo-l,4-dihydro-2H”3,l-benzoxazin-2-one as a colorless solid (4.7g, 21 mmol, 77percent).

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. 20712-12-3, (2-Amino-5-bromophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SANOFI-AVENTIS; NAKAYAMA, Kazuki; SAKAI, Daiki; WATANABE, Kazutoshi; KOHARA, Toshiyuki; ARITOMO, Keiichi; WO2011/19090; (2011); A1;,
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Application of 14320-38-8, 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.

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 to room 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*200 mL). The combined organics were washed sequentially with water (3*300 mL) and saturated aqueous sodium chloride solution (2*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) provided tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane (188 g, 98%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 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).

The chemical industry reduces the impact on the environment during synthesis 14320-38-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; Siu, Michael; Estrada, Anthony; Liu, Wen; Lyssikatos, Joseph P.; Patel, Snahel; Liang, Guibai; Chen, Kevin; US2015/175619; (2015); A1;,
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Application of 575-03-1, 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 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a magnetically-stirred solution of 7-hydroxycoumarin derivatives (2 mmol), aromatic aldehydes (2 mmol) and NEt3 (2 mmol) in THF (8 mL) a mixture of dialkyl acetylenedicarboxylate (2 mmol) in THF (2 mL) was added in 15 min. The reaction mixture was then allowed to stand at room temperature for 0.5-10 h. After completion of the reaction as indicated by thin-layer chromatography (TLC) (n-hexane/EtOAc, 1:1), the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (Merck, 230-400 mesh) using a mixture of n-hexane/EtOAc (1:1) as eluent to afford the pure product as a light yellow powder.

According to the analysis of related databases, 575-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Asghari, Sakineh; Baharfar, Robabeh; Darabi, Samaneh Ahangar; Mohammadian, Reza; Journal of the Brazilian Chemical Society; vol. 26; 2; (2015); p. 218 – 223;,
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Adding a certain compound to certain chemical reactions, such as: 4704-94-3, 2-(Hydroxymethyl)propane-1,3-diol, 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, 4704-94-3, blongs to alcohols-buliding-blocks compound. Safety of 2-(Hydroxymethyl)propane-1,3-diol

To a solution of 2-(hydroxymethyl)propane-l,3-diol (1 g) in THF (20 mL) were added 2,2-dimethoxypropane (1.344 mL) and para-toluenesulfonic acid monohydrate (0.054 g). The reaction mixture was stirred at room temperature for 4 hours, treated with TEA and concentrated. The concentrate was purified by flash chromatography (Analogix SF25chi40g with 20-30percent ethyl acetate/hexanes). MS (ESI) m/z 147.0 (M+l)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4704-94-3, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/129385; (2009); A1;,
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Electric Literature of 13330-96-6 , The common heterocyclic compound, 13330-96-6, name is 4-(Dimethylamino)butan-1-ol, molecular formula is C6H15NO, 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.

Example 36; 2-Butoxy-8-hydroxy-9-{3-[(4-dimethylaminobutoxy)carbonylmethyl]benzyl}adenine; 2-Butoxy-8-hydroxy-9-(3-carboxymethylbenzyl)adenine (88mg, 0.24mmol)which was prepared in Reference example 76 was suspended in DMF (10ml). Thereto were added at 0C 4-dimethylaminobutanol (0.16 ml, 1.18mmol), 1-hydroxybenzotriazole (0.16g, 1.18mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23g, 1.18 mmol) in this order and the mixture was stirred at room temperature for 6 hours. After removal of the solvent by an evaporator, an aqueous saturated sodium bicarbonate solution was added to this residue and the resulted precipitate was filtered, followed by washing with water to give the titled compound as a white solid (73mg, 0.16mmol). Yield: 65% 1H NMR(DMSO-d6)delta 9.97(1H, brs), 7.20(4H, m), 6.45(2H, brs), 4.82(2H, s), 4.14(2H, t, J = 6.6 Hz), 4.00(2H, t, J = 6.6 Hz), 3.62(2H, s), 2.11(2H, t, J = 7.0 Hz), 2.04(6H, s), 1.62(2H, m), 1.51 (2H, m), 1.36(4H, m), 0.90(3H, t, J = 7.4 Hz).

The synthetic route of 13330-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1728792; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 100058-61-5, 3-(Benzyloxy)cyclobutanol, 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, 100058-61-5, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

To a solution of 3-benzyloxycyclobutanol (5.0 g, 28.0 mmol) in dichloromethane (40 mL)was added dropwise diethylaminosulfur trifluoride (7.41 mL, 56.1 mmol) at 0 C. Thereaction was stirred at 15 C for 16 h and quenched with ice water (50 mL). Saturated aqueous sodium bicarbonate was added (100 mL), and the mixture was extracted with dichloromethane (200 mL). The organic phase was washed with brine (100 mL), dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography (eluting gradient: 10% ethyl acetate in petroleum ether) to give (3- fluorocyclobutoxy)methylbenzene (1.30 g, 26%) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100058-61-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian C.; DO, Steven; DROBNICK, Joy; GOBBI, Alberto; KATSUMOTO, Tamiko; KIEFER, JR., James Richard; LIANG, Jun; RAJAPAKSA, Naomi S.; CHEN, Yongsheng; FU, Liqiang; LAI, Kwong Wah; LIU, Zhiguo; WAI, John; WANG, Fei; (322 pag.)WO2018/234345; (2018); A1;,
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