1: NaI / acetone / 70 h / Heating 2: 54 percent / Na2CO3 / acetonitrile / 18 h / Heating 3: 85 percent / H2 / Pd/C / acetic acid / 15 h / 60 °C / 2280 Torr 4: 1.) K2CO3, 2.) LiAlH4 / 1.) THF, 2.) RT, 18 h View Scheme

1: 83 percent / thionyl chloride / pyridine / Ambient temperature 2: NaI / acetone / 70 h / Heating 3: 54 percent / Na2CO3 / acetonitrile / 18 h / Heating 4: 85 percent / H2 / Pd/C / acetic acid / 15 h / 60 °C / 2280 Torr 5: 1.) K2CO3, 2.) LiAlH4 / 1.) THF, 2.) RT, 18 h View Scheme

1: 54 percent / Na2CO3 / acetonitrile / 18 h / Heating 2: 85 percent / H2 / Pd/C / acetic acid / 15 h / 60 °C / 2280 Torr 3: 1.) K2CO3, 2.) LiAlH4 / 1.) THF, 2.) RT, 18 h View Scheme

1: 85 percent / H2 / Pd/C / acetic acid / 15 h / 60 °C / 2280 Torr 2: 1.) K2CO3, 2.) LiAlH4 / 1.) THF, 2.) RT, 18 h View Scheme

formic acid

1: 42 percent / lithium aluminium hydride / tetrahydrofuran / 24 h / Heating 2: 92 percent / formic acid View Scheme

lithium aluminium tetrahydride; potassium carbonate 1.) THF, 2.) RT, 18 h; Yield given. Multistep reaction;