63366-79-0

105-37-3

63366-79-0

A solution of dimethylacetamide (18 mL) of nitroethane (1.7 mL, 24 mmol) was slowly added to a methanolic solution of 0.5 M sodium methanol (48 mL, 24 mmol) under nitrogen protection. After the reaction mixture was cooled to 50 °C, acetyl chloride (1.7 mL, 24 mmol) and ethyl propionate (2.4 mL, 24 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 20 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently partitioned between water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give an orange oily crude product (3.7 g). The crude product was purified by fast column chromatography (eluent: 10% ethyl acetate/hexane) to afford methyl 3-methyl-5-isoxazolecarboxylate as white crystals (900 mg, 24% yield).