Hydrochloric Acid → Dimethyl (4-methoxy-2-nitrobenzyl)malonate

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[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([C:17]([O:19][CH3:20])=[O:18])[C:13]([O:15][CH3:16])=[O:14])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:17]([O:19][CH3:20])=[O:18])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1

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실험 절차

Sodium borohydride (3.36 g) was added to a methanol (200 ml) solution of dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate (25 g) under ice-cooling. The reaction mixture was stirred at room temperature for one hour and then neutralized by adding dropwise 1N aqueous hydrochloric acid solution. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous potassium bicarbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to obtain the entitled compound (19 g).