[F:1][C:2]1[C:3]([CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:4]([C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[O:22]([NH2:24])[CH3:23].C([O-])(=O)C.[Na+]>C(O)C>[F:1][C:2]1[C:3]([CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:4]([C:8](=[N:24][O:22][CH3:23])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1To a solution of 79 g (0.28 mole) of ethyl 3-fluoro-2-[(1,1-dimethylethoxy)methyl]-α-oxo-benzeneacetate in 300 mL of ethyl alcohol was added 100 mL (0.39 mole, 30% aq) of methoxylamine HCl followed by 33 g (0.4 mole) of sodium acetate. The mixture was then heated at 60° C. for three hours. After cooling to room temperature, the salts were filtered and the mixture was concentrated in vacuo. Water and EtOAc were added, the layers separated, and the organics were washed with saturated NaHCO3, brine and dried over MgSO4. After filtration, the solution was concentrated in vacuo to give 86.1 g of ethyl 3-fluoro-2-[(1,1-dimethylethoxy)methyl]-α-(methoxyimino)-benzeneacetate as a lightly tinted oil, 1:2 ratio of oxime isomers by gas chromatography.
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