tri-ruthenium(0)dodecacarbonyl; sodium formate; lithium chloride T=150°C; 24 h; AutoclaveIonic liquid;

in hexane 2 h;

1: ethanol / Heating 2: KOH / ethanol 3: 175 °C 4: 87 percent / LiAlH4 / diethyl ether / Heating View Scheme

1: 91 percent / CH2Cl2 / 16 h / Ambient temperature 2: 77 percent / Na, liq. NH3 / tetrahydrofuran; ethanol / 3 h / -33 °C View Scheme

PPh3.Br2 in dichloromethane T=0 - 10°C; Bromination;

1: pyridine / 1 h / 0 °C 2: LiBr / acetone / 5 h / Heating 4: KOH / ethanol; H2O / 5 h / Heating 5: 83 percent / N2H4*H2O, KOH / bis-(2-hydroxy-ethyl) ether; methanol / 125 deg C, 6 h; 195 deg C, 3 h View Scheme

pyridine-SO3 complex; dimethyl sulfoxide; triethylamine in dichloromethane T=0 - 20°C;

copper(II) oxide T=235°C; 23 h;

1: 60 percent / I2, chlorodiphenylphosphine, imidazole / toluene / 3 h / 70 °C 2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -78 deg C to RT, 1 h, 2.) THF, hexane, form -78 deg C to RT, 4 h 3: 68 percent / methanolic para-toluenesulfonic acid / toluene / 144 h 4: 88 percent / H2 / 10percent Pd/C / diethyl ether / 16 h 5: 44 percent / molecular sieves 4 A, pyridinum dichromate / dimethylformamide / 120 h / Ambient temperature 6: 94 percent / 10percent aq. tetrabutylammonium hydroxide / CH2Cl2 / 16 h View Scheme