C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1.[CH3:18][O:19][N:20]=[C:21]([C:29]1[O:30][CH2:31][CH2:32][N:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28].[OH-].[Na+]>CN(C=O)C>[CH3:18][O:19][N:20]=[C:21]([C:29]1[O:30][CH2:31][CH2:32][N:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1DMF (2.2 ml), potassium carbonate (210 mg, 1.5 mmol) and 2-chloro-5-trifluoromethylpyridine (220 mg, 1.2 mmol) were added to 2-hydroxyphenyl 2-oxazolin-2-yl ketone O-methyloxime (220 mg, 1.0 mmol), and the mixture was at 100° C. for 2.5 hours. After completion of the reaction, 1N NaOH (100 ml) was added, and the mixture was extracted with ether. The ether layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(5-trifluoromethyl-2-pyridyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime (190 mg, 52.1%) as an oil.
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