反应详情

Dissolve (Z)-2-bromo-3-cyclohexyl-acrylic acid ethyl ester (76.4 g, 300 mmol) and 4-(methylthio)benzene boronic acid (60.5 g, 360 mmol) in a mixture of 1500 mL toluene, 500 mL ethanol and 2M aqueous sodium carbonate solution (500 mL). Add tetrakis(triphenylphosphino)palladium(0) (10.4 g, 3mol %) and heat the mixture at reflux for 5 h. Cool and remove the ethanol under vacuum. Partition the residue between water (250 mL) and dichloromethane (4×250 mL). Combine the extracts and dry over magnesium sulfate, filter and concentrate. Pass through a silica gel pad with a mix of iso-hexane:dichloromethane:diethyl ether (92:4:4) to give the title compound as a hazy oil (80 g). GC-MS (m/e): 304 (M+).

1. temperatureat reflux for 5 h
2. temperatureCool
3. customremove the ethanol under vacuum
4. customPartition the residue between water (250 mL) and dichloromethane (4×250 mL)
5. dry with materialCombine the extracts and dry over magnesium sulfate
6. filtrationfilter
7. concentrationconcentrate
8. additionPass through a silica gel pad with a mix of iso-hexane:dichloromethane:diethyl ether (92:4:4)