Hydroxyamine hydrochloride → Ethyl 5-cyclopropylisoxazole-4-carboxylate

Participants

Reaction Steps

A mixture of hydroxylamine hydrochloride (105.0 g. 1.51 mole), ethyl β-cyclopropyl-α-ethoxymethylene-β-ketopropionate (320.0 g., 1.51 mole) [prepared in Step A], and 1200 ml of ethanol was refluxed for 2 h. The solvent was removed in vacuo and the residue was partitioned between water and ether. The organic phase was separated, washed again with water, dried and evaporated to leave a dark, greasy solid. Trituration of the crude product under Skellysolve B gave 158 g of the title compound.

Provenance & Evidence