Multi-step reaction with 7 steps
1: 2.) H2O2, NaOH / 1.)Et2O, rt, overnight, 2.) MeOH, H2O, rt, 2 h
2: 76 percent / NaH / dimethylformamide / 2 h
3: 100 percent / DIBAL-H / tetrahydrofuran / 2 h / Heating
4: 13 percent / dimethylsulfoxide / 2 h / 70 °C
5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, -78 deg C, 1 h, 23 deg C, 1 h
6: PCC / CH2Cl2 / Ambient temperature
7: 70 percent / NaN3, H2SO4 / hexane / 0 deg C, 2 h, rt, 2 d
With
sodium hydroxide; n-butyllithium; sodium azide; sulfuric acid; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo961723x