Toluene → 2-[4-[[2-(2-Furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]-3-pyridinecarbaldehyde

Participants

Reaction Steps

To a mixture of 3-cyano-2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine (6.30 g) and anhydrous toluene (250 mL) was dropwise added a solution (0.95 M, 47 mL) of diisobutylaluminum hydride in hexane at −78° C. The reaction mixture was allowed to warm to room temperature with stirring for 1 hr. A saturated aqueous ammonium chloride solution (50 mL) was dropwise added to the reaction mixture at 0° C. and ethyl acetate was further added. Insoluble materials were filtered off and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals (1.0 g, yield 16%) of 2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]-3-pyridinecarbaldehyde from a fraction eluted with ethyl acetate-hexane (2:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 120-121° C.

Provenance & Evidence