1: 97.6 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 95 percent / CH2Cl2 / 2 h / Heating 3: 84.4 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C 4: 88.7 percent / HCl gas / ethanol / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether

1: 97.6 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 95 percent / CH2Cl2 / 2 h / Heating 3: 88 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C 4: HCl / ethanol / Ambient temperature View Scheme