Dicyclohexylcarbodiimide → HCID 18993837, compound

Participants

Reaction Steps

2.6 g of N,N'-dicyclohexylcarbodiimide were added while stirring within 5 minutes to a solution of 1.2 g of 4-cyano-3-fluorophenol, 1.2 g of 4-[(E)-but-2-enoyloxy]benzoic acid and 0.1 g of 4-(dimethylamino)pyridine in 50 ml of dichloromethane. The reaction mixture was stirred overnight, then filtered. The filtrate was washed with saturated sodium bicarbonate solution and with water and concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) and two-fold recrystallization of the fractions which were pure according to thin-layer chromatography gave 2.0 g of 4-cyano-3-fluorophenyl 4-[(E)-but-2-enoyloxy]benzoate. M.p. (C-N) 125° C. and cl.p. (N-I) 195° C.

Provenance & Evidence