lithium aluminium tetrahydride in diethyl ether T=22°C; 18 h;

1: 60 percent / pyridine / 5 h / Heating 2: 71 percent / sodium hydride / dimethylsulfoxide / 1.) below 40 deg C, 20 min, 2.) 22 deg C, 45 min 3: 91 percent / acetic anhydride / diethyl ether / 16 h / 22 °C 4: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 5: 79 percent / potassium carbonate / dimethylformamide / 2 h / 100 °C 6: 86 percent / LiAlH4 / diethyl ether / 18 h / 22 °C View Scheme

1: 71 percent / sodium hydride / dimethylsulfoxide / 1.) below 40 deg C, 20 min, 2.) 22 deg C, 45 min 2: 91 percent / acetic anhydride / diethyl ether / 16 h / 22 °C 3: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 4: 79 percent / potassium carbonate / dimethylformamide / 2 h / 100 °C 5: 86 percent / LiAlH4 / diethyl ether / 18 h / 22 °C View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 2: 79 percent / potassium carbonate / dimethylformamide / 2 h / 100 °C 3: 86 percent / LiAlH4 / diethyl ether / 18 h / 22 °C View Scheme

1: 91 percent / acetic anhydride / diethyl ether / 16 h / 22 °C 2: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 3: 79 percent / potassium carbonate / dimethylformamide / 2 h / 100 °C 4: 86 percent / LiAlH4 / diethyl ether / 18 h / 22 °C View Scheme

1: 79 percent / potassium carbonate / dimethylformamide / 2 h / 100 °C 2: 86 percent / LiAlH4 / diethyl ether / 18 h / 22 °C View Scheme