[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11][OH:12])[N:10]=1.Cl[C:15]1[N:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1.CN(C)C=O.[H-].[Na+]>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11][O:12][C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=2)[N:10]=1To a mixture of [2-(2-furyl)-5-methyl-4-oxazolyl]methanol (5.18 g), 6-chloro-3-cyanopyridine (4.00 g) and N,N-dimethylformamide (100 ml) was added sodium hydride (60% in oil, 1.27 g) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography, and 6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]nicotinonitrile was obtained as colorless crystals (6.97 g, yield 86%) from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 105–106° C.
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