Multi-step reaction with 10 steps
1: 17.25 g / NaH / tetrahydrofuran; hexane; diethyl ether / 40 h / Ambient temperature
2: 96 percent / DIBAL / CH2Cl2 / -78 deg C, 1 h, then 0 deg C
3: CBr4, Ph3P / CH2Cl2 / 1 h / -78 °C
4: 3.10 g / toluene / 12 h / Heating
5: 66 percent / NaH / CH2Cl2 / 1 h / Ambient temperature
6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h
7: 100 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C
8: 94 percent / NaI / acetone / 4 h / 50 °C
9: 47 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature
10: 78 percent / 1.)BuLi / 1.) THF, -78 deg C to 0 deg C, 20 min, 2.) THF, -78 deg C, 30 min, then 0 deg C, 30 min
With
n-butyllithium; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetone; toluene;
DOI:10.1016/S0040-4020(01)85090-0