Dicyclohexylcarbodiimide → 2-(4-Hexylphenyl)-5-(4-allylcarbonyloxyphenyl)-1,3-thiazole

Participants

Reaction Steps

30 ml of dichloromethane was added to 2.0 g (5.93 mM) of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)-1,3-thiazole and 0.52 g (6.16 mM) of vinylacetic acid, followed by stirring at room temperature to the mixture, 1.21 g (5.86 mM) of N,N'-dicyclohexylcarbodiimide (DCC) and 0.02 g of 4-pyrrolidinopyridine were added, followed by stirring for 5 hours at room temperature. The resultant dicyclohexylurea was recovered by filtration, followed by washing with dichloromethane to be added to the filtrate. The resultant dichloromethane solution was condensed into a solid under reduced pressure, followed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent of ethanol/ethyl acetate to obtain 1.93 g of 2-(4-hexylphenyl)-5-(4-allylcarbonyloxyphenyl)-1,3-thiazole (Yield: 81.1%).

Provenance & Evidence