[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14](OC)=[O:15])[N:13]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:7][CH:8]=1A solution of methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxylate (1.365 mmol) in tetrahydrofuran (20 ml) was cooled to 0° C., and lithium aluminum hydride in tetrahydrofuran (1.365 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, slowly quenched with water, followed by addition of ammonium chloride solution. The resulting mixture was filtered through celite, and washed with ethyl acetate. The filtrate was washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by chromatography, to yield {2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methan-1-ol, a compound of formula (16).
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