[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH:23]([CH3:25])[CH3:24]>CC(C)=O.C(Cl)Cl>[CH3:24][CH:23]([O:10][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)[CH3:25]To a stirred mixture of 3.6 g (0.02 mole) of 5-nitro-2-(1H-pyrrol-1-yl)phenol and 3.7 g (0.27 mole) of potassium carbonate in 40 ml of acetone was added 4.5 g (0.027 mole) of 2-iodopropane. After complete addition the mixture was stirred at reflux for approximately 16 hours. The reaction mixture was cooled, and the solvent evaporated under reduced pressure to leave a residue. The residue was dissolved in methylene chloride, filtered, and the filtrate evaporated under reduced pressure to leave residue. The residue was purified by column chromatography on silica gel, eluting with toluene, to yield 3.5 g of 1-(1-methylethoxy-4-nitrophenyl)pyrrole (mp 59°-61° C.).
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