S(O)(O)(=O)=O.[NH2:6][OH:7].C([O-])(=O)C.[Na+].O.[CH2:14]([O:18][CH2:19][CH:20]=O)[CH2:15][CH:16]=[CH2:17]>C(O)C>[CH2:14]([O:18][CH2:19][CH:20]=[N:6][OH:7])[CH2:15][CH:16]=[CH2:17]
Hydroxylamine sulfate (20.5 g), sodium acetate (12.8 g) and water (20 ml) were added to a solution of 3-butenyloxyacetaldehyde (17.8 g; J. Chem. Soc., Perkin Trans. 1, 1999, 3143-3155) in ethanol (200 ml). The mixture was stirred at room temperature overnight and then water was added. The excess of ethanol was evaporated under reduced pressure and the resulting residue was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (6.20 g).
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