Dicyclohexylcarbodiimide → 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentylthiophene

Participants

Reaction Steps

Dicyclohexylcarbodiimide (0.2 g) was added to a solution of 2-(4-hydroxyphenyl)-5-pentylthiophene (0.25 g), (E)-hex-2-enoic acid, (0.1 g) 4-(dimethyiamino)pyridine (0.05 g) and dichloromethane (20 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down. The residue was purified by column chromatography on silica gel using hexane/ethyl acetate (9/1 v/v) as eluent and recrystallisation from hexane to yield 0.17 g of 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentylthiophene, K 47° C., [N 46° C.], I.

Provenance & Evidence