反应详情

温度

100 °C

A partial solution of 7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (495 mg, 1.26 mmol) in anhydrous toluene (6.3 mL) was purged with N2, treated with dichlorobis(triphenylphosphine)palladium(II) (177 mg, 0.25 mmol), purged with N2, and treated with tributyl(1-ethoxyvinyl)tin (0.600 mL, 1.9 mmol). The resulting mixture was stirred under a N2 atmosphere and heated in an oil bath at 100° C. for two hours. After cooling to room temperature, the mixture was filtered through a pad of silica gel, washing the product off with EtOAc. The filtrate and washings were evaporated under vacuum to an oil. The crude product was purified by flash chromatography on a Biotage 40S KP-Sil column, eluting with 4:1 hexanes-EtOAc (1 L) followed by 2:1 hexanes-EtOAc (1 L). The product containing fractions were concentrated under vacuum to afford 7-(acetylamino)-9a-butyl-4-(1-ethoxyvinyl)-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (238 mg, 49%) as a yellow foam.

1. custompurged with N2
2. temperatureAfter cooling to room temperature
3. filtrationthe mixture was filtered through a pad of silica gel
4. washwashing the product off with EtOAc
5. customThe filtrate and washings were evaporated under vacuum to an oil
6. customThe crude product was purified by flash chromatography on a Biotage 40S KP-Sil column
7. washeluting with 4:1 hexanes-EtOAc (1 L)
8. additionThe product containing fractions
9. concentrationwere concentrated under vacuum