C([O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=2)[N:9]=[N:8][N:7]=1)(=O)C.[Li+].[OH-]>CCO.O>[OH:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=2)[N:9]=[N:8][N:7]=1To a solution of 1-[4-cyano-3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 22, 45 g) in EtOH and water (2:1) was added LiOH (8.21 g, 0.342 mol) at 0° C. The reaction was stirred for 3 hours at room temperature. The solvent was removed under vacuum and the residue diluted with DCM, washed with ice-water, saturated aqueous NaHCO3 and brine. The solution was dried over anhydrous Na2SO4 and the solvent removed under vacuum. The crude product was purified by triturating with ether (500 mL) to yield 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile as a viscous oil (30 g).
불러오는 중…