[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=1.[BH4-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:15]([O:17][CH3:18])=[O:16])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=1To a solution of dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate (25 g) in methanol (200 ml) was added sodium borohydride (3.36 g) in an ice bath. After stirring at room temperature for 1 hr, the reaction mixture was neutralized by adding 1 N aqueous hydrochloric acid. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate:hexane=1:4) to obtain the titled compound (19 g).
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