[N+]([O-])([O-])=[O:2].[Tl+].[CH2:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][CH2:9][CH2:8]1>CO.C(Cl)(Cl)Cl>[CH3:18][O:17][CH:14]1[CH2:13][CH2:12][C:11]2=[CH:10][CH:9]=[CH:8][C:6](=[O:2])[CH2:7][CH:16]2[CH2:15]1To a solution of thallium nitrate (2.4 g) in methanol (24 ml) was added 1-methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene (1.0 g) in methanol (7 ml) in one portion. The mixture was stirred for 1 minute and diluted with chloroform (24 ml). The resulting precipitate was filtered off and the filtrate was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution; 8:1, n-hexane-ethyl acetate) to give 3-methoxy-1,2,3,4-tetrahydro-5H-benzocyclohepten-6-one (0.78 g).
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