hydrogenchloride in tetrahydrofuran; water Cooling with ice;

1.1: hydrogenchloride / water; tetrahydrofuran / |Cooling with ice 2.1: triethylamine / ethanol / 1 h / 20 °C / |Inert atmosphere 2.2: 4 h / |Inert atmosphere; |Reflux 3.1: palladium hydroxide on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 4.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 4.2: 0.25 h / 20 °C 5.1: lithium tri-t-butoxyaluminum hydride / diethyl ether / 4 h / 0 °C View Scheme

1.1: hydrogenchloride / water; tetrahydrofuran / |Cooling with ice 2.1: triethylamine / ethanol / 1 h / 20 °C / |Inert atmosphere 2.2: 4 h / |Inert atmosphere; |Reflux 3.1: palladium hydroxide on carbon; hydrogen / ethanol / 12 h / 20 °C / 760.05 Torr 4.1: sodium iodide / acetonitrile / 0.25 h / 20 °C 4.2: 0.25 h / 20 °C 5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0 °C View Scheme