反应详情

A stirred, cooled (0° C.) solution of N-(3-bromo-phenyl)-N-methyl-formamide (Intermediate 112, 2.6 g, 9.7 mmol) and titanium tetra-iso-propoxide (3.9 mL, 10.67 mmol) in tetrahydrofuran (40 mL) was treated with a 3M solution of ethyl magnesium bromide in ether (8.08 mL, 24.25 mmol) under argon and the resulting reaction mixture was allowed to warm to ambient temperature gradually and refluxed at 55° C. overnight. It was then cooled in an ice-bath, quenched with saturated aqueous ammonium chloride solution, filtered over celite and the aqueous phase was extracted with diethyl ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil. Flash column chromatography over silica gel (230-400 mesh) using 1.5% ethyl acetate in hexane as the eluent afforded the title compound (0.321 g, 15%).

1. customthe resulting reaction mixture
2. temperaturerefluxed at 55° C. overnight
3. temperatureIt was then cooled in an ice-bath
4. customquenched with saturated aqueous ammonium chloride solution
5. filtrationfiltered over celite
6. extractionthe aqueous phase was extracted with diethyl ether
7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customevaporated in vacuo
10. customto afford an oil