Multi-step reaction with 6 steps
1: 67 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 22 h / Ambient temperature
2: DIBAH / CH2Cl2 / 1 h / -78 °C
3: 1.) Et3B, CF3SO2H, 2.) iPr2NEt, 3.) aq. H2O2 / 1.) CH2Cl2, hexane, 0 deg C, 30 min, 2.) -78 deg C, 3 h; room temperature, 4 h, 3.) MeOH, room temperature, 1 h
4: 98 percent / iPr2NEt / CH2Cl2 / 0.5 h / 0 °C
5: 72 percent / LiBH4 / ethanol / 2 h / 0 °C
6: 100 percent / PPh3, imidazole, iPr2NEt, I2 / diethyl ether; benzene / 0.5 h
With
1H-imidazole; lithium borohydride; triethyl borane; trifluoromethanesulfinic acid; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/jo981370x