palladium diacetate; triethylamine; triphenylphosphine in N,N-dimethyl-formamide T=50°C; P=750.075 Torr; 24 h; Inert atmosphereReflux; chemospecific reaction;

sulfuric acid in methanol; hexane

diethyl ether

1: 1.) formic acid, 30 percent hydrogen peroxide; 2.) 20 percent H2SO4 / 1.) 35 deg C, 2 h, room temp., 12 h; 2.) reflux, 10 h 2: 93 percent / NaH / benzene / 5 h / 65 - 70 °C 3: NaBH4 / methanol / 4 h / Ambient temperature 4: p-toluenesulfonic acid / 1.) room temp., 1h; 2.) 65 deg C, 6 h View Scheme

1: 93 percent / oxalic acid / H2O / 6 h / Heating 2: 1.) formic acid, 30 percent hydrogen peroxide; 2.) 20 percent H2SO4 / 1.) 35 deg C, 2 h, room temp., 12 h; 2.) reflux, 10 h 3: 93 percent / NaH / benzene / 5 h / 65 - 70 °C 4: NaBH4 / methanol / 4 h / Ambient temperature 5: p-toluenesulfonic acid / 1.) room temp., 1h; 2.) 65 deg C, 6 h View Scheme

1: NaBH4 / methanol / 4 h / Ambient temperature 2: p-toluenesulfonic acid / 1.) room temp., 1h; 2.) 65 deg C, 6 h View Scheme

1: 93 percent / NaH / benzene / 5 h / 65 - 70 °C 2: NaBH4 / methanol / 4 h / Ambient temperature 3: p-toluenesulfonic acid / 1.) room temp., 1h; 2.) 65 deg C, 6 h View Scheme

1: triethylamine; hydrazine hydrate / methanol / 2.5 h / |Reflux 2: iodine; N,N,N',N'-tetramethylguanidine / diethyl ether / 0.5 h / 20 °C / |Cooling with ice 3: triethylamine; palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 24 h / 50 °C / 750.08 Torr / |Inert atmosphere; |Reflux View Scheme

toluene-4-sulfonic acid 1.) room temp., 1h; 2.) 65 deg C, 6 h; Yield given. Multistep reaction;