N-(4-{2-[5-(1,3-dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide → N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide

Participants

Reaction Steps

N-(4-{2-[5-(1,3-Dioxolan-2-yl)-4-methylthiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (4.42 g, 13.1 mmol) was dissolved in a mixture of ethyl acetate (400 ml) and acetic acid (100 ml), and 10% palladium carbon (2.21 g, containing 50% water) was added. The mixture was hydrogenated at room temperature under an atmospheric pressure. The reaction mixture was filtered through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6) to give N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide (2.26 g, 7.68 mmol, yield 58.4%) as a yellow solid.

Provenance & Evidence