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

Temperature

65 °C

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).

1. customTo a 25 mL RB flask fitted with a magnetic stirrer
2. additionAfter addition
3. customAfter completion of the reaction
4. washthe organic layer was washed with saturated NaHCO3 solution (10 mL), thiosulfate solution (10 mL), water (25 mL) and finally with brine solution (10 mL)
5. dry with materialThe organic layer was dried over anhydrous Na2SO4
6. customthe solvent was removed under reduced pressure

ORD record

ord-71fd92b7c1c24bddbb7f7a9aafb779c4

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2