lithium aluminium tetrahydride in tetrahydrofuran T=0 - 50°C; Inert atmosphere;

lithium aluminium tetrahydride in diethyl ether 8 h; Heating;

in diethyl ether

1: potassium carbonate; sodium iodide / dichloromethane / 16 h / |Reflux; |Inert atmosphere 2: thionyl chloride / dichloromethane / 2 h / 20 °C / |Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 16 h / 20 °C / |Inert atmosphere 4: sulfuric acid / 144 h / 60 °C / |Inert atmosphere 5: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 50 °C / |Inert atmosphere View Scheme

1: sulfuric acid / 144 h / 60 °C / |Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 50 °C / |Inert atmosphere View Scheme

1: 24.9 percent / acetonitrile / 30 h / Heating 2: 100 percent / lithium aluminum hydride / diethyl ether / 8 h / Heating View Scheme