反应详情

In 560 ml of ethanol was dissolved 25 g (1.08 eq.) of sodium and a mixture of 135.6ml (146 g; 1 mol) of diethyl oxalate and 116.7 ml (120 g; 1 mol) of acetophenone was added thereto dropwise at 40° C. One hour later, reflux was begun and it was continued for 30 minutes. The solvent was distilled off. The residue was neutralized with sulfuric acid (55 g/water 200 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane 1:1), to give colorless plates. The crystals were recovered by filtration with ethyl acetate/hexane. Yield: 114.6 g.

1. additionwas added
2. customdropwise at 40° C
3. temperatureOne hour later, reflux
4. distillationThe solvent was distilled off
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
8. distillationThereafter, the solvent was distilled off
9. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane 1:1)
10. customto give colorless plates
11. filtrationThe crystals were recovered by filtration with ethyl acetate/hexane