Multi-step reaction with 7 steps
1: LiAlH4 / diethyl ether / 1 h / Ambient temperature
2: PBr3 / diethyl ether / 1 h
3: 58 percent / ethanol / 1 h / Heating
4: aq. NaIO4 / methanol / 6 h / Ambient temperature
5: KMnO4 / methanol; H2O / 0.5 h / Ambient temperature
6: 84 percent / NBS, azobis(isobutyronitrile) / CCl4 / 2 h / Heating; Irradiation
7: 1.) LDA, HMPT, 2.) / 1.) THF, 0 deg C, 1 h, 2.) -78 deg C, 0.5 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); phosphorus tribromide; lithium diisopropyl amide;
In
methanol; tetrachloromethane; diethyl ether; ethanol; water;
DOI:10.1021/jo00323a016