Tetrahydrofuran → {3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}acetonitrile

참여 물질

반응 단계

To a mixture of potassium tert-butoxide (0.94 g) and dimethoxyethane (30 mL) was added p-toluenesulfonyl methylisocyanide (0.86 g) at −78° C., and a solution of 3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde (1.96 g) in dimethoxyethane (50 mL)-tetrahydrofuran (10 mL) was added at −78° C. After stirring at the same temperature for 1 hr, the reaction mixture was heated to room temperature. Methanol (30 mL) was added to the obtained mixture, and the mixture was heated under reflux for 1 hr. After cooling, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give {3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}acetonitrile as colorless crystals (1.21 g, yield 61%) from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 153-154° C.

출처 및 근거