Multi-step reaction with 7 steps
1: 86 percent / (NH4)2SO4 / 1.) 100 deg C, 5 h; 125 deg C, 19 h, 2.) TMSCl was added to complete conversion at 25 deg C, then 125 deg C, 12 h
2: 1.) n-BuLi, 2.) hexachloroethane / 1.) ether, hexane, 25 deg C, 24 h, 2.) ether, hexane, -40 deg C, 1 h
3: 83 percent / (NH4)2SO4 / 1.) 100 deg C, 5 h; 125 deg C, 19 h, 2.) TMSCl was added to complete conversion at 25 deg C, then 125 deg C, 12 h
4: 1.) n-BuLi, 2.) hexachloroethane / 1.) ether, hexane, 0 deg C, 40 min, 2.) ether, hexane, -40 deg C, 1 h
5: 1.) 1,1'-carbonyldiimidazole / 1.) THF, 25 deg C, 20 h, 2.) THF, 25 deg C, 20 h
6: 95.3 percent / BH3*THF, BF3*Et2O / 6 h / Heating
7: 99 percent / DMAP, NEt3 / CH2Cl2 / 27 h / 25 °C
With
dmap; ammonium sulfate; n-butyllithium; borane-THF; hexachloroethane; boron trifluoride diethyl etherate; triethylamine; 1,1'-carbonyldiimidazole;
In
dichloromethane;
DOI:10.1021/ja00195a044