C(Cl)(=O)C(Cl)=O.[O:7]1[C:11]2[CH2:12][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[OH:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:14][CH2:15][C:10]=2[CH:9]=[CH:8]1.C(N(CC)CC)C>ClCCl.CS(C)=O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([S:16]([N:13]2[CH2:14][CH2:15][C:10]3[CH:9]=[CH:8][O:7][C:11]=3[CH2:12]2)(=[O:17])=[O:18])=[CH:20][CH:21]=1)(=[O:26])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1To a solution of 0.04 ml (0.5 mmol) of oxalyl chloride in 30 ml of dichloromethane, 0.07 ml (1.0 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 0.122 g (0.330 mmol) of 4-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-ylsulfonyl)phenylphenylmethanol in 10 ml of dichloromethane and 1 ml of dimethyl sulfoxide was added at -78° C., followed by stirring for 15 minutes. To this mixture, 0.28 ml (2.0 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. After the reaction mixture was washed with water, the water layer was re-extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to yield the desired product.
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