Water → 2-Benzoyl-1-[3,3-di(ethoxycarbonyl)propyl]pyrrole

Participants

Reaction Steps

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.

Provenance & Evidence