Butanal → 1-(But-1-enyl)pyrrolidin-2-one

Participants

Reaction Steps

A solution of 2-pyrrolidone (50 g, 0.588 mol), butanal (42.4 g, 0.588 mol) and P2O5 (2 g, 0.014 mol) in 300 ml toluene, were refluxed together for 10 hours using Dean-Stark apparatus to collect liberated water. The resulting solution was cooled and washed with 5% solution of sodium bicarbonate and dried over anhydrous sodium sulphate. After removing the solvent under reduced pressure, 1-(but-1-enyl)pyrrolidin-2-one (I) was obtained by distillation as a liquid. (68.2 g, 83.2%). 1H NMR (CDCl3): δ 1.02 (3H, t), 2.03-2.15 (4H, m), 2.45 (2H, t), 3.5 (2H, t), 5.01 (1H, m), and 6.85 (1H, d). 13C-NMR (CDCl3): δ 172.52, 122.91, 113.8, 45.09, 31.07, 23.03, 17.27, and 14.27. IR: 2962, 2930, 1698, 1663, 1253 Cm−1.

Provenance & Evidence