O.OS(O)(=O)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:23])[CH2:20][CH2:21][OH:22])[N:18]=2)[CH:11]=[CH:12][CH:13]=1.CC([OH:27])C>CC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:23])[CH2:20][C:21]([OH:27])=[O:22])[N:18]=2)[CH:11]=[CH:12][CH:13]=1A mixture of CrO3 (0.46 g, 4.63 mmol), H2O (2.5 mL) and concentrated H2SO4 (0.46 mL) was added to a solution of 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butan-1-ol (0.9 g, 3.6 mmol) in acetone (30 mL) at 0° C. The reaction was stirred at r.t. for 1.5 h. 2-Propanol was added and the mixture was concentrated. Sat. NaCl (25 mL) and EtOAc (50 mL) were added to the residue and the mixture was extracted. The water phase was re-extracted with EtOAc (50 mL) and the combined organic phases were dried (MgSO4) and concentrated to give 0.95 g (100%) of the title compound.
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