反应详情

温度

-78 °C

1H NMR (CDCl3, 400 MHz) δ: 3.65 (3H, m); 4.15 (2H, m); 6.1-6.2 and 6.4-6.7 (2H, m); 7-7.95 (7H, m). n-Butyl lithium (1.6 M solution in ether, 30 ml) was added at −78° C. and under argon atmosphere to a solution of N-methylimidazole (3.2 ml; 40 mmol). After stirring at −78° C. for 45 minutes, zinc iodide (14 g; 44 mmol) in solution in THF (100 ml) was added. The mixture was allowed to warm to ambient temperature for 1 hour, cooled down to −78° C., and a solution of copper (I) cyanide (0.72 g; 8 mmol) and lithium chloride (0.68 g; 1.6 mmol) in THF (10 ml) was then added at −78° C. followed by a solution of methyl 2-(4-fluorophenyl)-4-(3-bromoprop-1-en-1-yl)benzoate (7 g; 20 mmol) in THF (50 ml). The mixture was stirred at −78° C., for 30 minutes and for 1 hour 30 minutes at room temperature. After evaporation of the solvent, the residue was treated with EDTA (17 g; 44 mmol) in distilled water (50 ml) and extracted with dichloromethane. The organic layer was evaporated and purified by flash chromatography eluting with dichloromethane/ethanol (98/2) to give methyl 4-[3-(1-methylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate as a mixture of E and Z isomers. Yield: 71%

1. temperatureto warm to ambient temperature for 1 hour
2. temperaturecooled down to −78° C.
3. stirringThe mixture was stirred at −78° C., for 30 minutes and for 1 hour 30 minutes at room temperature
4. customAfter evaporation of the solvent
5. extractionextracted with dichloromethane
6. customThe organic layer was evaporated
7. custompurified by flash chromatography
8. washeluting with dichloromethane/ethanol (98/2)