4-Toluenesulfonyl chloride → Ethyl 2-(p-toluenesulfonyloxyimino)-2-cyanoacetate

Participants

Reaction Steps

In ethyl acetate (50 ml) are dissolved ethyl 2-hydroxyimino-2-cyanoacetate (7.1 g) and triethylamine (7.0 ml). To the solution is added p-toluenesulfonyl chloride (9.5 g) with stirring under ice-cooling, and the mixture is stirred for 2 hours and allowed to stand overnight. The reaction mixture is filtered and the filtrate is concentrated. To the residue is added cyclohexane and the resulting crystals are separated by filtration and dried to give ethyl 2-(p-toluenesulfonyloxyimino)-2-cyanoacetate (13.9 g), melting point: 84°-87° C.

Provenance & Evidence