[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@@H:9]1[CH2:11][C@H:10]1[C:12](=O)[CH3:13].N1C=CC=CC=1.Cl.[CH3:22][O:23][NH2:24]>CO.O>[CH3:22][O:23][N:24]=[C:12]([C@@H:10]1[CH2:11][C@H:9]1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:13]To a stirred solution of trans 1-[2-(2-Chloro-6-fluoro-phenyl)-cyclopropyl]-ethanone (1.0 g; 4.7 mmol) in methanol (10 ml) at ambient temperature was added pyridine (0.60 ml; 7.0 mmol) and methoxyamine hydrochloride (0.60 g; 7.0 mmol). The reaction mixture was stirred for 16 hours at ambient temperature then poured in water (50 ml) and extracted with dichloromethane (3×30 ml). Combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed in vacuo to afford 1.1 g (100% of theory) of trans 1-[2-(2-Chloro-6-fluoro-phenyl)-cyclopropyl]-ethanone O-methyl-oxime as an E/Z mixture in form of an oil.
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