N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide → N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[C].[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide (932.3 mg, 3.58 mmol) in ethyl acetate (50 ml) was added 10% palladium carbon, and the mixture was hydrogenated at room temperature and atmospheric pressure. After the completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, dichloromethane:methanol=40:1→20:1) to give N-{4-[2-(4-hydroxyphenyl)ethyl]-1,3-thiazol-2-yl}acetamide (771.3 mg, 2.94 mmol, yield 82.1%) as a white solid.