[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([OH:22])C(C3C=CC=CC=3)O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]=[O:22])=[N:9]2)[CH:5]=[CH:6][CH:7]=11-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-2-phenyl-ethane-1,2-diol (50.0 mg, 0.158 mmol) was weighed into a vial and toluene (3 ml) was added. Potassium carbonate (47.0 mg, 0.340 mmol) and lead (IV) acetate (70.0 mg, 0.158 mmol) were added with stirring. The reaction was allowed to stir for 2.5 hours. The reaction was filtered and ethyl acetate was added to the filtrate and an aqueous workup was done. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (40% EtOAc/Hexanes) to yield the pure product as a white solid (22.3 mg, 68%). 1H NMR (CDCl3) δ (ppm): 10.34 (s, 1H); 8.27 (s, 1H); 8.14 (m, 1H); 7.575 (d, 2H).
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