Multi-step reaction with 9 steps
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: 68 percent / K2CO3, DBU / acetone / 2 h / 60 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; sodium periodate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); nickel; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jo00323a016