N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane 1.5 h; HeatingIrradiation;

phosphorus tribromide in diethyl ether 1 h;

1: LiAlH4 / diethyl ether / 1 h / Ambient temperature 2: PBr3 / diethyl ether / 1 h View Scheme

1: 58 percent / ethanol / 1 h / Heating 2: aq. NaIO4 / methanol / 6 h / Ambient temperature 3: KMnO4 / methanol; H2O / 0.5 h / Ambient temperature 4: 84 percent / NBS, azobis(isobutyronitrile) / CCl4 / 2 h / Heating; Irradiation 5: 1.) LDA, HMPT, 2.) / 1.) THF, 0 deg C, 1 h, 2.) -78 deg C, 0.5 h 6: Raney nickel / ethanol; acetone / 1 h / 60 °C 7: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 8: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme