Hydroxylamine HCl → HCID 19971654, compound

A mixture of the above ketone (8.8 g, 46 mmol), hydroxylammonium chloride (5.5 g, 78 mmol) and anhydrous pyridine (50 ml) was heated at reflux for 16 h. The reaction mixture was allowed to cool to room temperature and the solvent then evaporated in vacuo. To the residue was added 10% aqueous citric acid (100 ml) and the mixture was extracted with ethyl acetate (100 ml+50 ml). The combined organic phases were washed with 10% aqueous citric acid (25 ml), brine (25 ml) and dried (Na2SO4). The solvent was evaporated in vacuo and the residue purified by column chromatography on silica gel (250 g, n-heptane/ethyl acetate gradient 1/4 to 1/2 to give 7.25 g of Z-5-methoxy-1-phenyl-1-pentanone oxime as a colourless oil.