C[O:2][C:3](=O)[CH2:4][C:5]1[C:6]([CH3:21])=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C(OCC)(=O)C>[CH3:21][C:6]1[C:5]([CH2:4][CH2:3][OH:2])=[CH:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:13][CH:12]=2)[N:7]=1
2.6 g (8.40 mmol) of [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester in 15 ml of dry tetrahydrofuran were added under an argon atmosphere within 15 minutes to a stirred suspension of 0.38 g (10 mmol) of lithium aluminium hydride in 5 ml of tetrahydrofuran. The reaction was exothermic. Subsequently, the mixture was stirred at room temperature for 1 hour. Then, 1 ml of ethyl acetate was dropped to the reaction mixture, followed by water, drop after drop, under argon, with stirring and cooling until the gas evolution ceased. The reaction mixture was diluted with 50 ml of ethyl acetate, dried with anhydrous sodium sulfate and filtered. The filtrate was evaporated and the residue was chromatographed on silicagel with a mixture of dichloromethane and tert.-butyl methyl ether (4:1 vol./vol.) as eluent. 1.88 g (79.5% of theory) of 2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol was obtained as white solid.
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