Acetic Acid → 1,3-Diethyl 2-[(2-cyanoeth-1-EN-1-YL)amino]propanedioate

Participants

Reaction Conditions

Reaction Steps

Into a 500-mL round-bottom flask was placed isoxazole (25 g, 354.76 mmol, 1.00 equiv, 98%) in ethanol (100 mL) and sodium ethanolate (124 mL, 21%). The resulting solution was stirred at 0° C. for 30 min. Then acetic acid (6.9 mL, 98%), sodium acetate (20.5 g, 244.91 mmol, 0.69 equiv, 98%) and diethyl 2-aminomalonate hydrochloride (48 g, 222.26 mmol, 0.63 equiv, 98%) were added. The resulting solution was allowed to react, with stirring, for an additional 48 h at room temperature, concentrated under vacuum, dissolved in 200 mL of dichloromethane, washed with 2×100 mL of water, dried over anhydrous sodium sulfate and concentrated to afford 30 g (37%) of diethyl 2-(2-cyanovinylamino)malonate as a yellow oil

Provenance & Evidence