[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]([CH3:18])=[O:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>O1CCOCC1.O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([CH:16]([OH:17])[CH3:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]To a stirring mixture of 22 g (0.090 mole) of methyl 5-(p-acetamido-phenyl)-2-furyl ketone and 345 ml of 95% dioxane/H2O was added portionwise 3.4 g (0.090 mole) of NaBH4 while maintaining the temperature at 15°-20°. The resulting mixture was stirred overnight at room temperature and then added to ice/water. The solid was filtered and dried at 60° to yield 21 g (95%), m.p. 175°-177°, of title compound.
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