Trifluoroacetic acid → 3-Isoxazolecarboxylic acid, 4-iodo-5-methyl-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a 25 mL RB flask fitted with a magnetic stirrer was charged with 1 mL of TFA. To the stirred solvent were added ethyl 5-methyl-1,2-oxazole-3-carboxylate (0.1 g, 0.6 mmol) and N-iodosuccinimide (0.289 g, 1.2 mmol). After addition, the reaction mixture was heated at 65° C. for 3 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 mL), the organic layer was washed with saturated NaHCO3 solution (10 mL), thiosulfate solution (10 mL), water (25 mL) and finally with brine solution (10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as a brown liquid (0.12 g, yield: 66.2%). 1H NMR (300 MHz, CDCl3): δ 4.36-4.43 (q, 2H), 2.49 (s, 3H), 1.34-1.39 (t, 3H).

Provenance & Evidence