反应详情

温度

100 °C

To a mixture of 5-(3-Bromo-phenyl)-isoxazole-3-carboxylic acid methyl ester (1.5 g, 5.3 mmol), Pd(OAc)2 (60 mg, 0.27 mmol), P(o-tolyl)3 (162 mg, 0.53 mmol) in anhydrous N,N-dimethylformamide (15 mL) in a pressure tube was added 3-buten-2-ol (0.92 mL, 10.6 mmol) and triethylamine (1.1 mL, 7.95 mmol). The mixture was flushed with nitrogen for 3 minutes, capped and heated to 100° C. for 30 minutes. The reaction mixture was allowed to cool to ambient temperature, partitioned between ethyl acetate and water (75 mL, 1:1). The organic layer was washed with brine (2×25 mL), dried (Na2SO4), filtered, concentrated under reduced pressure and purified on a Silica Gel MPLC eluting with 20–40% ethyl acetate/hexanes to provide the titled compound as a light yellow solid (860 mg, 59%). MS (ESI(+)) m/e 274 (M+H)+.

1. customThe mixture was flushed with nitrogen for 3 minutes
2. customcapped
3. temperatureto cool to ambient temperature
4. custompartitioned between ethyl acetate and water (75 mL, 1:1)
5. washThe organic layer was washed with brine (2×25 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. custompurified on a Silica Gel MPLC
10. washeluting with 20–40% ethyl acetate/hexanes