Diethyl Oxalate → Ethyl N,N-diethyloxamate

Participants

Reaction Conditions

Reaction Steps

To 30.00 g (203.2 mmol) diethyloxalate (7) were added at room temperature 42.2 mL diethylamine (406.4 mmol, 2.0 eq). The colorless clear solution was heated to reflux (oil bath temperature: 90° C.) and the reaction was monitored by HPLC. After 2.5 h, the resulting yellow-orange liquid was cooled to room temperature and all volatile compounds (ethanol, diethylamine) were removed in a rotary evaporator (50° C., 10 mbar) furnishing the crude product (35.073 g, 100% by weight) as a yellow liquid. Purification was achieved using a high vacuum distillation (bp 85° C. at 0.08 mbar) furnishing the title compound (30.22 g, 174.4 mmol, 86% by weight) as colorless liquid.

Provenance & Evidence