Multi-step reaction with 7 steps
1: thionyl chloride / 1.) room temperature, 45 min, 2.) 45 deg C, 2 h
2: 91 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature
3: 82 percent / dimethylsulfoxide / 1 h / Ambient temperature
4: 70.5 percent / zinc, acetic acid / dimethylformamide / 0.75 h / 0 °C
5: thionyl chloride / dimethylformamide / 4 h / 40 - 45 °C
6: 79 percent / pyridine / diethyl ether / 30 h / Heating
7: 1.) sodium hydride, 2.) 1,2-bis(diphenylphosphino)ethane / 2.) tetrakis(triphenylphosphine)palladium(0) / 1,) THF, 0 deg C, 30 min; room temperature, 15 min, 2.) reflux
With
pyridine; thionyl chloride; sodium hydride; acetic acid; 1,2-bis-(diphenylphosphino)ethane; zinc;
tetrakis(triphenylphosphine) palladium(0);
In
diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja00534a030