Multi-step reaction with 6 steps
1: 1) n-BuLi / 1) Et2O, hexane, 0 deg C to room temperature; reflux, 24 h, 2) Et2O, hexane, -78 deg C to room temperature; room temperature, 2 h
2: 112.6 g / 10percent H2SO4 / diethyl ether; hexane
3: 95 percent / PBr3 / diethyl ether / 2 h / Ambient temperature
4: 80 percent / various solvent(s) / 5.5 h / 80 - 100 °C
5: 1) n-BuLi / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C to room temperature
6: 1) n-BuLi / 1) THF, hexane, -78 deg C to room temperature, 2) THF, hexane, -78 deg C to room temperature
With
n-butyllithium; sulfuric acid; phosphorus tribromide;
In
diethyl ether; hexane;
DOI:10.1021/jo970592c