Water → 1,4-Diethyl 2-formylbutanedioate

Participants

Reaction Steps

To a mixture of sodium (1.66 g, 72.13 mmol) in diethyl ether (35 mL) was added diethyl succinate (10 mL, 60.11 mmol) and ethyl formate (8.25 mL, 102.18 mmol) at room temperature, and the reaction mixture was refluxed for 5 hours. After the cooling to room temperature, water was added to the mixture until the sodium salt was dissolved completely and aqueous layer was separated. The aqueous layer was neutralized by 6M hydrochloric acid (10.8 mL) and extracted with diethyl ether. The extracts were washed with sat.NaHCO3, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by distillation (115-120° C., 10 mmHg) to give diethyl 2-formylsuccinate (6.55 g, 54%) as colorless oil.

Provenance & Evidence