Toluene → {4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanol

Participants

Reaction Steps

To a solution of methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate (1.34 g, 2.90 mmol) in tetrahydrofuran (10 mL) was added dropwise a toluene solution (1.0 M, 6.38 mL, 6.38 mmol) of diisobutylaluminum hydride under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, sodium sulfate 10 hydrate was added, and the mixture was further stirred for 1 hr. The insoluble material was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-60:40) to give the title compound (0.950 g, yield 75%) as a colorless oil.

Provenance & Evidence