反应详情

Ethyl 4-acetylbenzate (5.00 g, 26.0 mmol) was added to a solution (130 ml) of ethyl diethylphosphonoacetate (6.71 ml, 33.8 mmol) and tert-butoxy potassium (4.38 g, 39.0 mmol) in tetrahydrofuran at 0° C., and the mixture was stirred at room temperature for 16 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate). The mixture of the obtained oil and 10% palladium carbon (1 g) in ethanol (150 ml) was stirred under a hydrogen atmosphere for 2 hrs, and filtered through celite. The solvent was evaporated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate) to give the title compound (5.67 g).

1. washthe mixture was washed with saturated brine
2. dry with materialdried over anhydrous sodium sulfate
3. customThe solvent was evaporated under reduced pressure
4. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)
5. additionThe mixture of the obtained oil and 10% palladium carbon (1 g) in ethanol (150 ml)
6. stirringwas stirred under a hydrogen atmosphere for 2 hrs
7. filtrationfiltered through celite
8. customThe solvent was evaporated under reduced pressure
9. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)