[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[N:13][C:12]=1[CH2:26][CH2:27][CH2:28][CH3:29])=O.[Cl-].[NH4+].Cl>O1CCCC1>[CH2:26]([C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[S:15][C:11]=1[CH2:9][OH:8])[CH2:27][CH2:28][CH3:29]To a solution of lithium aluminium hydride (1.2 g) in dry tetrahydrofuran (100 mL) add 4-butyl-2-(4-trifluormethyl-phenyl)-thiazol-5-carboxylic acid methyl ester (5.3 g, 15.4 mmol) dissolved in tetrahydrofuran (100 mL). Stir the reaction mixture at room temperature over a period of one hour. Add a saturated aqueous solution of ammonium chloride (50 mL) and then a 1 molar aqueous solution of hydrochloric acid (50 mL). Extract the reaction mixture five times with portions of 60 ml of ethyl acetate. Dry the combined extracts with MgSO4 and remove the solvent under reduced pressure to provide [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol (4.6 g) as a yellow oil, which solidified upon standing at room temperature.
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