Malononitrile → 2-(1-Ethoxypropylidene)malononitrile

Participants

Reaction Steps

Heat a mixture of triethyl orthopropionate (446 g, 2.53 mol) and malononitrile (163.9 g, 2.48 mol) at reflux under nitrogen for 1.5 h. Cool the mixture and stir overnight. Distill the dark mixture under vacuum (10-15 torr, 135-142° C.) to afford the title compound as a pale yellow oil: 1H NMR (CDCl3) δ 4.40 (q, J=7.0, 2H), 2.63, (q, J=7.7, 2H), 1.41 (t, J=7, 3H), 1.23 (t, J=7.7, 3H); 13C NMR (CDCl3) 189.7, 113.3, 111.8, 68.3, 64.1, 25.5, 14.6, 11.3.

Provenance & Evidence