nickel in ethanol; acetone 1 h; Heating;

1: azobis(isobutyronitrile), NBS / CCl4 / 1.5 h / Heating; Irradiation 2: 58 percent / ethanol / 1 h / Heating 3: aq. NaIO4 / methanol / 6 h / Ambient temperature 4: KMnO4 / methanol; H2O / 0.5 h / Ambient temperature 5: 84 percent / NBS, azobis(isobutyronitrile) / CCl4 / 2 h / Heating; Irradiation 6: 1.) LDA, HMPT, 2.) / 1.) THF, 0 deg C, 1 h, 2.) -78 deg C, 0.5 h 7: Raney nickel / ethanol; acetone / 1 h / 60 °C 8: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 9: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme

1: PBr3 / diethyl ether / 1 h 2: 58 percent / ethanol / 1 h / Heating 3: aq. NaIO4 / methanol / 6 h / Ambient temperature 4: KMnO4 / methanol; H2O / 0.5 h / Ambient temperature 5: 84 percent / NBS, azobis(isobutyronitrile) / CCl4 / 2 h / Heating; Irradiation 6: 1.) LDA, HMPT, 2.) / 1.) THF, 0 deg C, 1 h, 2.) -78 deg C, 0.5 h 7: Raney nickel / ethanol; acetone / 1 h / 60 °C 8: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 9: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme

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 8: Raney nickel / ethanol; acetone / 1 h / 60 °C 9: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 10: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme

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

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

1: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 2: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme

1: Raney nickel / ethanol; acetone / 1 h / 60 °C 2: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 3: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme

1: 1.) LDA, HMPT, 2.) / 1.) THF, 0 deg C, 1 h, 2.) -78 deg C, 0.5 h 2: Raney nickel / ethanol; acetone / 1 h / 60 °C 3: 81 percent / sodium hydride / tetrahydrofuran; dimethylsulfoxide / 1 h / Ambient temperature 4: 72 percent / Raney nickel / acetone; ethanol / 1 h / Heating View Scheme