Ethyl propiolate → HCID 131711223, compound

Participants

Reaction Steps

1.5 g (0.0079 mole) of 5-methoxy-3-diazooxindole and 0.99 g (0.01 mole of 1.3 equiv.) of 99% ethyl propiolate are refluxed in benzene (50 ml) under N2 for 24 hours. The reaction mixture is cooled down to room temperature and the precipitates that form are filtered off and washed well with ether, dried in a vacuum oven at 60° for 2 hours. Yield: 661.8 mg, m.p. 202°-204°, Rf 0.3. This crude product is taken up in 75 ml of absolute ethanol, treated with activated carbon, filtered through a celite pad and the clear filtrate is concentrated down to a volume of ~50 ml on the steam bath. After cooling, the precipitates that form are filtered off. The product is dried overnight in a vacuum oven at room temperature. Yield: 555.4 mg, m.p. 225°-227°.

Provenance & Evidence