Sodium hydride → 5-{(E)-2-[4-(benzyloxy)-3-methylphenyl]ethenyl}-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

Participants

Reaction Steps

To a stirred solution of diethyl {4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methylphosphonate (intermediate 4, 1.4 g) in dry tetrahydrofuran (10 ml) cooled in ice under nitrogen was added sodium hydride (0.12 g, 60% dispersion in mineral oil) and the reaction was stirred for 30 minutes. A solution of 4-benzyloxy-3-methylbenzaldehyde (0.724 g) in dry tetrahydrofuran (10 ml) was added drop-wise, the reaction was allowed to come to room temperature and stirred for 2 hours. The solvent was removed and the residues partitioned between water (50 ml) and chloroform (50 ml). The aqueous phase was extracted with chloroform (20 ml) and the combined organics were washed with water and dried. Removal of solvent gave a solid which was purified by SPE chromatography. Elution with cyclohexane:ethyl acetate (20:1) gave the title compound as a yellow solid.

Provenance & Evidence