O.[OH-].[Li+].C([O:7][CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([C:24]#[N:25])[CH:15]=2)[N:12]=[N:11][N:10]=1)(=O)C>C(O)C.O.CCOC(C)=O>[OH:7][CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([CH:15]=2)[C:24]#[N:25])[N:12]=[N:11][N:10]=1Lithium hydroxide monohydrate (1.35 g, 32.2 mmol) was added to a solution of {1-[3-cyano-4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 39, 5.0 g, 16.1 mmol) in a mixture of ethanol and water (2:1) at 0° C. The reaction mixture was stirred for 6 h at room temperature. The reaction mixture was diluted with EtOAc and washed with ice-water. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-60% EtOAc/pet.ether to give the title compound (1.2 g).
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