lithium aluminium tetrahydride in diethyl ether 20 h; Ambient temperature;

1: 90 percent / CF3CO2H / CH2Cl2 2: 1.) DPPA / 1.) toluene, 80 deg C 3: 1.) TBAF, 2.) LiAlH4 / 1.) THF, 2.) THF View Scheme

1: 65.7 percent / KOH / ethanol / 20 h / Ambient temperature 2: 89.4 percent / SOCl2 / toluene / 2 h / Heating 3: NaN3 / H2O; acetone / 0.5 h / 0 °C 4: benzene / 0.5 h / Heating 5: 73 percent / LiAlH4 / diethyl ether / 20 h / Ambient temperature View Scheme

1: NaN3 / H2O; acetone / 0.5 h / 0 °C 2: benzene / 0.5 h / Heating 3: 73 percent / LiAlH4 / diethyl ether / 20 h / Ambient temperature View Scheme

1: 89.4 percent / SOCl2 / toluene / 2 h / Heating 2: NaN3 / H2O; acetone / 0.5 h / 0 °C 3: benzene / 0.5 h / Heating 4: 73 percent / LiAlH4 / diethyl ether / 20 h / Ambient temperature View Scheme

1: 1.) DPPA / 1.) toluene, 80 deg C 2: 1.) TBAF, 2.) LiAlH4 / 1.) THF, 2.) THF View Scheme