[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH3:19])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]>CO>[CH3:19][CH:17]([OH:18])[C:15]1[O:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1Sodium borohydride (9.0 g, 0.34 mole) was added in portions to a stirred mixture of 55 g (0.24 mole) of methyl 5-(p-nitrophenyl)-2-furyl ketone in 700 ml of methanol at 20°-25° over 45 minutes. The mixture was stirred at ambient temperature for 4 hours and allowed to stand overnight. Some insoluble material was removed by filtration and discarded. The filtrate was poured into a mixture of ice and water (3 liters) and made acidific with 5% aqueous HCl. The brown oil which was deposited solidified on standing and was collected by filtration to give 56 g (100%) of title compound. Recrystallization from a cyclohexane-benzene mixture gave an analytical sample, m.p. 69.5°-70.5°.
読み込み中…