Tetrahydrofuran → 2-Ethoxycarbonyl-3-phenethyl-succinic acid diethyl ester

Participants

Reaction Steps

A solution of diethylmalonate (240.2 mg, 1.5 mmol) and NaH (43.2 mg, 1.8 mmol) in THF (3 ml) was stirred for one hour at room temperature under argon. 2-(4-Nitro-benzenesulfonyloxy)-4-phenyl-butyric acid ethyl ester (590 mg, 1.5 mmol) and DMPU (192.2 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for three days. The reaction was poured into H2O and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The product was purified by column chromatography (petroleumether/ethyl acetate, 4:1) to give 2-ethoxycarbonyl-3-phenethyl-succinic acid diethyl ester (274 mg, 52.1%).

Provenance & Evidence