反应详情

温度

100 °C

Trifluoro-methanesulfonic acid 2-cyclopent-3-enylmethyl-5-methoxy-phenyl ester (2.00 g, 5.95 mmol) was dissolved in DMF (10 mL) under a N2 atmosphere and treated with triethylamine (0.91 g, 8.92 mmol) and 1,3-bis(diphenylphosphino)propane (0.37 g, 0.89 mmol). This mixture was stirred and degassed (3 vacuum/N2 purge cycles), and then treated with palladium acetate (93 mg, 0.42 mmol). After stirring for 20 min. the mixture was warmed to 100° C. for 18 hours, cooled and poured into brine (30 mL). The resulting mixture was extracted with EtOAc (4×10 mL) and the combined organic layer was washed with sat. aq. NaHCO3 soin. (10 mL), H2O (10 mL), brine (10 mL), dried (MgSO4), filtered and evaporated to an oil. The oil was chromatographed on Silica gel (2%CH2Cl2/hexanes) to provide product as an oil (1.05 g, 95%). (TLC 10%EtOAc/hexanes Rf 0.52). 1H NMR (CDCl3) δ 6.94 (d, J=8.0 Hz, 1H), 6.68 (dd, J=8.0,2.8 Hz, 1H), 6.59 (d, J=2.8 Hz, 1H), 6.23 (dd, J=5.5,2.8 Hz, 1H), 5.79 (dd, J=5.5,2.6 Hz, 1H), 3.77 (s, 3H), 3.28 (m, 1H), 2.96-2.89 (m, 2H), 2.49 (d, J=15.5 Hz, 1H), 2.19 (m, 1H), 1.85 (d, J=10.5 Hz, 1H). 13C NMR (CDCl3) 158.94, 144.07, 138.95, 131.24, 131.21, 128.34, 111.73, 111.45, 55.22, 45.10, 40.18, 38.47, 29.49. GCMS m/e 188 (M+).

1. customdegassed
2. custom(3 vacuum/N2 purge cycles)
3. stirringAfter stirring for 20 min. the mixture
4. temperaturecooled
5. extractionThe resulting mixture was extracted with EtOAc (4×10 mL)
6. washthe combined organic layer was washed with sat. aq. NaHCO3 soin
7. dry with material(10 mL), H2O (10 mL), brine (10 mL), dried (MgSO4)
8. filtrationfiltered
9. customevaporated to an oil
10. customThe oil was chromatographed on Silica gel (2%CH2Cl2/hexanes)