Methanol → Methyl 2-(3-methylisoxazol-5-yl)acetate

Temperature

50 °C

To a 50 mL RB flask fitted with magnetic stirrer was charged with 10 mL of methanol. To the stirred solvent was added (3-methyl-1,2-oxazol-5-yl)acetic acid (1 g, 7 mmol), was added drop wise SOCl2 (1.25 g, 10.5 mmol) to the reaction mixture at 0° C. and stirred at 50° C. for 4 h. After completion of the reaction, the reaction mixture was concentrated to distill off the solvent; water (25 mL) was added and extracted with ethyl acetate (25 mL). The organic layer was washed with saturated NaHCO3 solution (10 mL) and 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 brown liquid (1 g, yield: 92%). 1H NMR (300 MHz, CDCl3): δ 6.03 (s, 1H), 3.73 (d, 2H), 3.69 (s, 3H), 2.23 (s, 3H).

1. customTo a 50 mL RB flask fitted with magnetic stirrer
2. customAfter completion of the reaction
3. concentrationthe reaction mixture was concentrated
4. distillationto distill off the solvent
5. additionwater (25 mL) was added
6. extractionextracted with ethyl acetate (25 mL)
7. washThe organic layer was washed with saturated NaHCO3 solution (10 mL) and brine solution (10 mL)
8. dry with materialThe organic layer was dried over anhydrous Na2SO4
9. customthe solvent was removed under reduced pressure

ORD record

ord-72bdaca1cb1d4376b22829b5a30417bf

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2