1: 75 percent / LiAlH4 / diethyl ether / 6 h / Ambient temperature 2: 80 percent / thionyl chloride / 0.42 h / Heating 3: 45 percent / sodium ethoxide / ethanol / 4.5 h / Heating 4: 86 percent / HBr, triethylamine / H2O; ethanol / 0.33 h / Heating View Scheme

1: 75 percent / LiAlH4 / diethyl ether / 6 h / Ambient temperature 2: 80 percent / thionyl chloride / 0.42 h / Heating 3: 45 percent / sodium ethoxide / ethanol / 4.5 h / Heating 4: 80 percent / HBr / H2O / 0.33 h / Heating View Scheme

1: 75 percent / LiAlH4 / diethyl ether / 6 h / Ambient temperature 2: 80 percent / thionyl chloride / 0.42 h / Heating View Scheme