1: 100 percent / LiAlH4 / diethyl ether / 4 h / Heating 2: 93 percent / PBr3 / diethyl ether / 3 h / Heating 3: 91 percent / LiAlH4 / diethyl ether / 18 h / Heating 4: 46 percent / HNO3 / CH2Cl2 / 1 h / 25 °C 5: 79 percent / H2 / 10 percent Pd/C / methanol / 25 °C / 800 - 900 Torr View Scheme