反应详情

To a solution of ethyl 3-(4-fluorophenyl)-3-oxopropionate (5.0 g, 24 mmol) in 1,2-dimethoxyethane (40 ml) was added sodium hydride (60% in oil, 576 mg, 24 mmol) under ice-cooling and the mixture was stirred at room temperature for 1 hr. To the reaction solution was dropwise added a solution of. 2-(bromomethyl)-5-(trifluoromethyl)furan (6 g, 26 mmol) in 1,2-dimethoxyethane (50 ml) and the reaction solution was stirred overnight at room temperature. The reaction solution was poured into water (200 ml), saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl 3-(4-fluorophenyl)-3-oxo-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate (4.5 g, 52%).

1. temperaturecooling
2. additionTo the reaction solution was dropwise added a solution of
3. additionwas added
4. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
5. washThe extract was washed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)