1: 61 percent / LiAlH4 / diethyl ether / 240 h / Heating 2: 58 percent / aq. Na2Cr2O7, H2SO4 / diethyl ether / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether 72 h; Heating;

1: 61 percent / LiAlH4 / diethyl ether / 240 h / Heating 2: 58 percent / aq. Na2Cr2O7, H2SO4 / diethyl ether / Ambient temperature 3: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 °C 4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) from -78 deg C to 0 deg C, b) 0 deg C, 2 h View Scheme

1: 61 percent / LiAlH4 / diethyl ether / 240 h / Heating 2: 58 percent / aq. Na2Cr2O7, H2SO4 / diethyl ether / Ambient temperature 3: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 °C 4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) from -78 deg C to 0 deg C, b) 0 deg C, 2 h View Scheme