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 100704-10-7, name is (2-Chloropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. 100704-10-7
Example N; To a stirred solution of 2-chloropyridine-4-methanol (143 mg, 1 mmol) in chloroform (10 ml) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (210 mul, 1.5 mmol) and methanesulfonyl chloride (90 mul, 1.2 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with (32) (297 mg, 1 mmol), powdered anhydrous potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol). DMF (5 ml) was then added to the mixture at room temperature and stirred for overnight. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:2)) to afford 120 mg (28%) a white foam. Recrystallization from chloroform/ether/hexane resulted in a white solid. m.p. 206-207 C.; 1H-NMR (200 MHz, CDCl3) delta 1.13(3H, d, J=6.9 Hz), 1.23 (3H, d, J=6.9 Hz), 2.18 (1H, m), 2.43 (3H, s), 4.51 (1H, d, J=16.4 Hz), 5.06 (1H, d, J=16.4 Hz), 6.91-6.96 (2H, m), 7.66 (1H, s), 7.70 (1H, s), 7.88 (1H, s), 8.19 (1H, d, J=0.8 Hz, 5.5 Hz), 8.98 (1H, s); m/z (EI) 422(M+); HRMS (EI) Calcd, 422.114525, Found 422.114568.; Example BL; To a stirred solution of 2-chloro-4-pyridinemethanol (144 mg, 1 mmol) in chloroform (10 ml) at 0 C. (ice bath), was added triethylamine (210 mul, 1.5 mmol) and methanesulfonyl chloride (90 mul, 1.2 mmol). After stirring for 1.5 hr., the mixture was diluted with dichloromethane, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo and mixed with 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (323 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), lithium iodide (134 mg, 1 mmol). Anhydrous DMF (5 ml) was then added into the mixture and stirred for overnight at room temperature. The mixture was evaporated in vacuo. The residue was dissolved in methanol-dichloromethane (1:9), filtered through celite pad, and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, methanol:chloroform (2:98)) to afford 174 mg (38%) of a white solid. m.p. 242-244 C.; 1H-NMR (200 MHz, CDCl3/CD3OD) delta 1.12(3H, d, J=6.8 Hz), 1.22 (3H, d, J=6.8 Hz), 2.28 (1H, m), 2.40 (3H, s), 4.55 (1H, d, J=17.0 Hz), 4.97 (1H, d, J=17.0 Hz), 6.03 (1H, d, J=16.6 Hz), 6.97-6.99 (2H, m), 7.39 (1H, d, J=16.6 Hz), 7.55 (2H, s), 7.71 (1H, s), 8.15 (1H, d, J=5.8 Hz); m/z (EI) 448(M+).
Statistics shows that 100704-10-7 is playing an increasingly important role. we look forward to future research findings about (2-Chloropyridin-4-yl)methanol.
Reference:
Patent; Guo, Hongyan; Kim, Choung U.; Kim, Hae Soo; Lee, Chong-Kyo; Lee, Ill Young; Mitchell, Michael L.; Son, Jong Chan; Xu, Lianhong; US2008/70920; (2008); A1;,
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