Toluene → 6-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinaldehyde

Participants

Reaction Steps

To a mixture of 6-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile (5.45 g) and anhydrous toluene (150 mL) was dropwise added a solution (0.95 M, 41.0 mL) of diisobutylaluminum hydride in hexane at −78° C. The reaction mixture was allowed to warm to room temperature with stirring for 1.5 hrs. A saturated aqueous ammonium chloride solution (100 mL) was dropwise added to the mixture, and the mixture was further stirred at room temperature for 30 min. Ethyl acetate was added to the mixture and the mixture was stirred at room temperature for 30 min. Insoluble materials were filtered away. The filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (4.30 g, 78%) of 6-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]nicotinaldehyde from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 120-121° C.

Provenance & Evidence