Nitrogen → Methyl 2-(acetoxymethyl)oxazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(chloromethyl)oxazole-4-carboxylate (Organic Process Research & Development 2001, 5, 37-44) (20.00 g, 113.91 mmol) in acetic acid (80 mL) was treated with acetic anhydride (8.0 mL) followed by sodium acetate (39.72 g, 484.14 mmol). The reaction mixture was stirred at 120° C. for 3 h. EA (400 mL) was added at rt and the suspension was neutralized with sat. aq. sodium carbonate. The layers were separated and the aq. layer was extracted with EA (2×400 mL). The combined org. layers were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white solid. LC-MS-conditions 06: tR=0.48 min, [M+H]+=200.41.

Provenance & Evidence