Acetic Acid → Ethyl (3,5-dimethylisoxazol-4-yl)acetate

Participants

Reaction Steps

A mixture of ethyl 3-acetyl-4-oxopentanoate (37.24 g, 0.2 mol), hydroxylamine hydrochloride (14.6 g, 0.21 mol), NaOAc (17.23 g, 0.21 mol) and ethanol (500 mL) was refluxed for 4 hours. The reaction mixture was filtered, the filtrate was concentrated in vacuo and the residue was heated in acetic acid (12.61 g, 0.21 mol) and toluene (300 mL) for 6 to 6.5 hours with the removal of water. The reaction mixture was filtered and the filtrate was concentrated in vacuo to afford a tan oil which crystallized on cooling. The product was collected by filtration and washed with ether to afford 1.26 g of ethyl 3,5-dimethyl-4-isoxazolylacetate, m.p. 180-182° C. Additional product was obtained by concentration of the ether filtrate and distillation of the residue at 69-81.5° C. and 0.05 mm Hg to afford a total of 31.18 g (85%).

Provenance & Evidence