1: 100 percent / aq. ethanol; diethyl ether 2: 1.) titanium tetrachloride, zinc dust / 1.) THF, CH2Cl2, 30 min., 2.) THF, CH2Cl2, RT, 2 h. 3: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 4 h 4: 84 percent / pyridinium chlorochromate / CH2Cl2 / 15 h / Ambient temperature View Scheme

1: tetrahydrofuran; diethyl ether / 1.) -70 deg C, 1 h, 2.) 0 deg C, 30 min 2: p-TsOH*H2O / toluene / 0.5 h / Heating 3: 76 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 4: 45 percent / p-TsOH*H2O / nitromethane / 0.08 h / 40 °C View Scheme