2-Acetylbenzofuran → 1-(2-Benzofuranyl)-1-(4-methyl-5-thiazolyl)ethanol

Reaction equation

C([Li])CCC.[CH3:6][C:7]1[N:8]=[C:9]([Si](C)(C)C)[S:10][CH:11]=1.[C:16]([C:19]1[O:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH:23]=1)(=[O:18])[CH3:17]>C(OCC)C>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH:23]=[C:19]1[C:16]([C:11]1[S:10][CH:9]=[N:8][C:7]=1[CH3:6])([OH:18])[CH3:17]

Participants

Procedure

n-Butyllithium (2.5M solution in hexane, 1 equivalent) was added dropwise to a solution of 4-methyl-2-trimethylsilylthiazole (1 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylbenzofuran (1 equivalent) in diethyl ether was added. After 1 hour the mixture was allowed to warm to room temperature and was then quenched by the addition of saturated aqueous sodium hydrogen carbonate. Work up in the normal fashion and column chromatography on silica gel then afforded the title compound.