Multi-step reaction with 11 steps
1: 91 percent / pyridine / 3 h / 40 °C
2: 76 percent / DBU / 5 h / 120 °C
3: 1.) BH3*SMe2, 2.) H2O2, aq. NaOH / 1.) THF, from 0 deg C to RT, 12 h, 2.) THF, from 0 deg C to RT, 0.5 h
4: 87 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 6 h / Ambient temperature
5: 85 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature
6: pyridinium chlorochromate, 3A molecular sieves, NaOAc / CH2Cl2 / 3 h / Ambient temperature
7: tetrahydrofuran / 2 h / -20 °C
8: 92 percent / pyridinium chlorochromate, 3A molecular sieves, NaOAc / CH2Cl2 / 3 h / Ambient temperature
9: 92 percent / Na2HPO4, 6percent Hg(Na) / tetrahydrofuran; methanol / 3 h / -40 °C
10: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) THF, hexane, from 0 deg C to RT, 2 h
11: 41 percent / Dowex 50Wx8 / methanol / 0.25 h / Ambient temperature
With
pyridine; sodium hydroxide; disodium hydrogenphosphate; n-butyllithium; dowex 50Wx8; dimethylsulfide borane complex; 3 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium acetate; sodium; pyridinium p-toluenesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; mercury;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0957-4166(95)00141-B