[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[O:9][C:10]([CH3:15])=[C:11]([CH2:13][OH:14])[N:12]=1.Cl[C:17]1[CH:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][N:18]=1.O1CCC[CH2:28]1>O.CN(C)C=O>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[O:9][C:10]([CH3:15])=[C:11]([CH2:13][O:14][C:17]2[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:28])=[O:24])[CH:20]=[CH:19][N:18]=2)[N:12]=1Sodium hydride (60%, oily, 2.88 g) was added to a mixture of 2-(2-furyl)-5-methyl-4-oxazolylmethanol (10.80 g), methyl 2-chloro-4-pyridinecarboxylate (10.30 g), tetrahydrofuran (100 ml) and N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-4-pyridinecarboxylate (2.86 g, yield 15%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 80–81° C.
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