Water → HCID 20333863, compound

Participants

Reaction Steps

8.7 g (0.2 mol) of sodium hydride are suspended in 100 ml of tetrahydrofuran and the suspension is stirred at room temperature for 90 minutes with 23.6 g (0.2 mol) of ethyl lactate. 9.5 g (0.18 mol) of acrylonitrile are then added dropwise at 60° C. and the mixture is refluxed for 90 minutes. The mixture is poured into 200 ml of water and washed twice with 100 ml of ether each time. The aqueous phase is adjusted to pH 1 with 2-N hydrochloric acid and extracted three times with 150 ml of ether each time. The dried and concentrated ether phases give 20.1 g (89%) of 4-cyano-2-methyltetrahydrofuran-3-one of boiling point 116°-118° C./14 mmHg; IR: 2250 (CN), 1780 (C=O); NMR (CDCl3): 1.37 ppm doublet (CH3); 3.4-4.9 ppm multiplet.

Provenance & Evidence