反应详情

To a solution of diethyl malonate (5.40 g, 33.8 mmol) in anhydrous N,N-dimethylformamide (50 mL) at 0° C. was added sodium hydride (60% in mineral oil, 1.35 g, 33.8 mmol). The reaction mixture was warmed and stirred at room temperature for 30 minutes. To this mixture was then added a solution of 1-(2-iodoethyl)-2-benzoylpyrrole (11.0 g, 33.8 mmol) in N,N-dimethylformamide (50 mL). The reaction mixture was stirred at room temperature for 16 hours. The mixture was poured into water (1000 mL) and extracted with ethyl acetate (3×300 mL). The ethyl acetate extracts were combined, washed with water (2×200 mL) and saturated aqueous sodium chloride (300 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to provide 9.85 g (82%) of 2-benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole.

1. temperatureThe reaction mixture was warmed
2. stirringThe reaction mixture was stirred at room temperature for 16 hours
3. extractionextracted with ethyl acetate (3×300 mL)
4. washwashed with water (2×200 mL) and saturated aqueous sodium chloride (300 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. customThe crude oil was purified by column chromatography on silica gel eluting with hexane/ethyl acetate