thionyl chloride; N,N-dimethyl-formamide in 1,2-dichloro-benzene T=70 - 80°C; 2 h;

potassium permanganate; tetrakis(triphenylphosphine) palladium(0) 1) dioxane, hexane, reflux, 2) H2O, reflux; Yield given. Multistep reaction;

1: 2) KMnO4 / 1) Pd(PPh3)4 / 1) dioxane, hexane, reflux, 2) H2O, reflux 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 69 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 2) KMnO4 / 1) Pd(PPh3)4 / 1) dioxane, hexane, reflux, 2) H2O, reflux 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min View Scheme

dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine T=130°C; P=52505.3 Torr; 18 h;