[CH2:1]([CH2:3]N)[OH:2].C1(C)C(C)=CC=CC=1.[Cl:13][C:14]1[CH:33]=[CH:32][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](=[N:29][O:30][CH3:31])[C:27]#[N:28])=[CH:16][CH:15]=1>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.O>[CH3:31][O:30][N:29]=[C:26]([C:27]1[O:2][CH2:1][CH2:3][N:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([Cl:13])=[CH:33][CH:32]=1Zinc acetate dihydrate (400 mg, 1.8 mmol), ethanolamine (975 mg, 15.9 mmol) and xylene (8 ml) were added to 2-(4-chlorobenzyloxy)-α-methoxyiminophenylacetonitrile (4.00 g, 13.3 mmol), and the mixture was stirred under reflux for 63 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give isomer A (1.31 g, 28.6%, as crystals) and isomer B (0.45 g, 9.8%, as crystals) of 2-(4-chlorobenzyloxy)phenyl 2-oxazolin-2-yl ketone O-methyloxime.
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