Acetone → 4-Cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohex-3-enecarbonitrile

Participants

Reaction Steps

A solution of 1-cyclopropylmethyl-4-cyclopropylmethylsulfanylcyclohex-3-enecarbonitrile (10.7 g, 43.1 mmol) in acetone (200 ml) was treated with a solution of oxone (79.4 g, 129 mmol) in water (300 ml) and the mixture heated under reflux for 1 h. The mixture was allowed to cool to ambient temperature and the pH of the mixture adjusted to 7 by the addition of saturated sodium hydrogen carbonate solution. The mixture was diluted with water (200 ml) and extracted with ethyl acetate (2×400 ml). The combined organic layer was washed with water (250 ml) and brine (200 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give a white solid (11.2 g, 93%). 1H NMR δ (ppm) (CDCl3): 6.91 (1H, s), 2.98-2.74 (4H, m), 2.66-2.53 (1H, m), 2.42-2.25 (2H, m), 1.71-1.67 (3H, m), 1.13-1.05 (1H, m), 0.97-0.87 (1H, m), 0.73-0.59 (4H, m), 0.45-0.35 (2H, m), 0.23-0.18 (2H, m).

Provenance & Evidence