反应详情

温度

25 °C

To a stirred solution of 5-bromo-2,3-dihydro-1H-inden-1-one (5 g, 23.7 mmol) in toluene were added vinylboronic anhydride pyridine complex (8.55 g, 35.54 mmol), Pd(PPh3)4 (0.1 g, 0.094 mmol), K2CO3 (22.88 g, 165.83 mmol). The resultant reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to 25° C. and filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with EtOAc and washed with H2O and brine. The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography (SiO2, 5% EtOAc in petroleum ether) afforded the title compound as a solid (1.8 g, 48%): 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J=7.2 Hz, 1H), 7.49 (br s, 1H), 7.44 (d, J=7.2 Hz, 1H), 6.82 (m, 1H), 5.90 (d, J=7.4 Hz, 1H), 5.42 (d, J=6.4 Hz, 1H), 3.20 (m, 2H), 2.70 (m, 2H); ESIMS m/z 159.06 ([M+H]−).

1. customThe resultant reaction mixture
2. temperaturewas heated
3. temperatureat reflux for 16 h
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with EtOAc
7. washwashed with H2O and brine
8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
9. concentrationconcentrated under reduced pressure
10. customThe obtained residue was purified by flash column chromatography (SiO2, 5% EtOAc in petroleum ether)