Br[CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]=[C:8]([S:19]([CH3:22])(=[O:21])=[O:20])[C:9]3[O:10][C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[C:13]=32)=[CH:5][C:4]=1[S:23]([CH3:26])(=[O:25])=[O:24].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>C(#N)C.O>[S:19]([C:8]1[C:9]2[O:10][C:11](=[O:18])[C:12]([CH3:16])([CH3:17])[C:13]=2[C:14]2[C:6](=[CH:5][C:4]([S:23]([CH3:26])(=[O:24])=[O:25])=[C:3]([CH2:2][N:27]3[CH:31]=[N:30][CH:29]=[N:28]3)[CH:15]=2)[CH:7]=1)([CH3:22])(=[O:20])=[O:21]A solution of 8-bromomethyl-4,7-dimesyl-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone in acetonitrile (5 ml) was treated with 1,2,4-triazole (0.2 g) and potassium carbonate (0.14 g), and the mixture was stirred under reflux for 18 h. The mixture was diluted with water, neutralised with glacial acetic acid and extracted with ethyl acetate, and the ethyl acetate extract was dried and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography, using methanol:ethyl acetate, 1:99 v/v as eluant, to give 4,7-dimesyl-1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2(1H)-naphtho[2,1-b]furanone, m.p. 263°-264° after recrystallisation from ethyl acetate.
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