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(E)-tert-butyl 3-(5-methylisoxazol-3-yl)acrylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
159a) (E)-tert-Butyl 3-(5-methylisoxazol-3-yl)acrylate To a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (9.74 g, 38.6 mmol) in tetrahydrofuran (THF) (120 mL), sodium hydride (1 .685 g, 42.1 mmol) was added. The reaction mixture was stirred at 0 C under N2 for 10 mins. Then a solution of 5- methylisoxazole-3-carbaldehyde (3.9g, 35.1 mmol) in THF (500 mL) was added by dropwise and the reaction was stirred at 0 C for 15 mins. Then water was added and extracted with ethyl acetate (3x). The combined organic layer was washed with water (2x), brine (2x), dried over Na2S04 and concentrated. The crude product was purified on silica gel chromatography (hexane:ethyl acetate = 1 :5) to obtain the title compound (E)- tert-butyl 3-(5-methylisoxazol-3-yl)acrylate (6g, 28.1 mmol, 80 % yield) as an oil. LC-MS m/z 209.9 (M+H)+, 1 .73 min (ret. time).