[CH3:1][O-:2].[Na+].[N+:4]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[C:17]#[C:18][Si](C)(C)C)[C:10]([O:12][CH3:13])=[O:11])([O-:6])=[O:5].[C:23]([OH:26])(=O)C>CO>[CH3:1][O:2][CH:18]([O:26][CH3:23])[CH2:17][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[N+:4]([O-:6])=[O:5]To a methanol solution of 2.92 g (54.1 mmol) of sodium methoxide was added 3.00 g (10.8 mmol) of methyl 3-nitro-4-trimethylsilylethynylbenzoate prepared above. The mixture was refluxed for 30 minutes. After cooling to 0° C., 5.52 g (54.1 mmol) of acetic acid was added to the reaction mixture and the solvent was then distilled off under reduced pressure. Ice water was poured onto the resulting residue followed by extraction three times with dichloromethane. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 2.40 g (82.4%) of methyl 4-(2,2-dimethoxyethyl)-3-nitrobenzoate.
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