1,3-Dichloroacetone → 4-chloromethyl-2-[(E)-styryl]thiazole

関与物質

反応手順

A mixture of thiocinnamamide (11.7 g), 1,3-dichloroacetone (9.10 g) and ethanol (145 ml) was heated for one hour under reflux. The reaction mixture was poured onto ice-water, neutralized with potassium carbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with diethyl ether-hexane (1:5, v/v), 4-chloromethyl-2-[(E)-2-phenylethenyl]thiazole (9.40 g, 66%) was obtained. Recrystallization from diethyl ether-hexane gave colorless plates, mp 88-89° C.

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