Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl (2E)-3-(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-3-methylthiophen-2-yl)-2-propenoate

Participants

Reaction Steps

To a solution of N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide (468.0 mg, 1.590 mmol) in chloroform (4.7 ml) was added dropwise a solution of methyl (triphenyl phosphoranylidene)acetate (797.4 mg, 2.385 mmol) in chloroform (2 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Merck 9385 60 g, ethyl acetate:dichloromethane=1:8) to give methyl (2E)-3-(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-3-methylthiophen-2-yl)-2-propenoate (591.6 mg, containing triphenylphosphineoxide) as a pale-yellow solid.

Provenance & Evidence