Ethyl 2,4-dioxovalerate → Ethyl 5-methylisoxazole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 100 mL RB flask fitted with a condenser and a magnetic stirrer was charged with 10.5 mL of ethanol. To the stirred solvent were added ethyl 2,4-dioxopentanoate (2.5 g, 15 mmol), hydroxylamine hydrochloride (1.09 g, 15 mmol) and sodium bicarbonate (1.32 g, 15 mmol). After addition, the reaction mixture was refluxed at 80° C. for 8 h under nitrogen atmosphere. After completion of the reaction, the solvent was evaporated from the reaction mixture. Ethyl acetate (50 mL) was added; organic layer was washed with water (50 mL), followed by brine solution (25 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as a colorless liquid (1 g, yield: 40.08%). 1H NMR (300 MHz, CDCl3): δ 6.34 (s, 1H), 4.33-4.40 (q, 2H), 2.43 (s, 3H), 1.32-1.37 (t, 3H).

Provenance & Evidence