Multi-step reaction with 9 steps
1: 84 percent / PCl3 / CHCl3 / 40 h / Ambient temperature
2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C
3: 83 percent / methanol / Ambient temperature
4: 1.) n-BuLi / 1.) THF, -78 to -50 deg C, 0.5 h, 2.) THF, room temp., 40 min
5: 93 percent / Na/Hg, Na2HPO4 / methanol / 6 h / Ambient temperature
6: 1.) n-BuLi / 1.) THF, -78 to -50 deg C, 40 min, 2.) THF, -50 deg C, 5 min, then room temp., 10 min
7: 1.) n-BuLi / 1.) THF, -78 to -50 deg C, 20 min, 2.) THF, room temp., 30 min
8: 80 percent / Bu4NF / tetrahydrofuran / 20 h / Ambient temperature
9: 97 percent / Et3N, 4-dimethylaminopyridine / CH2Cl2 / 1.5 h / Ambient temperature
With
dmap; sodium hydroxide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; phosphorus trichloride;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;
DOI:10.1021/jo9801770