Toluene → 2-[3-Methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde

関与物質

反応手順

To a mixture of 2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinonitrile (4.25 g) and toluene (150 mL) was dropwise added a solution (0.95 M, 23.0 mL) of diisobutylaluminum hydride in hexane at −78° C. After stirring for 1 hr the reaction mixture was warmed to room temperature and the mixture was further stirred for 1 hr. A saturated aqueous ammonium chloride solution (35 mL) was dropwise added to the mixture and the mixture was stirred at room temperature for 30 min. To the mixture was added ethyl acetate and the insoluble materials were filtered off. 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 2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde as crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless crystals (710 mg, 17%). melting point: 99-100° C.

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