[CH3:1][S-:2].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12].C(O)(=O)C>CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]([S:2][CH3:1])[CH2:10][N+:11]([O-:13])=[O:12])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]To a solution of sodium methanethiolate (0.62 g, 8.8 mmol) in methanol (20 ml), trans-3,4-dimethoxy-β-nitrostyrene (1.42 g, 8 mmol) was added and stirred at room temperature for 5 minutes. Further, acetic acid (0.46 ml) was added and stirred for 5 minutes. After evaporating methanol to a half amount under reduced pressure, water was added and extracted with dichloromethane and the organic layers were combined, washed with water and dried over sodium sulfate. The solvent was distilled out under reduced pressure and the residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to yield 2-(3,4-dimethoxyphenyl)-2-(methylthio)nitroethane (1.24 g, 60%).
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