lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether 1) 2 h, reflux, 2) 12 h, r.t.;

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / |Inert atmosphere 2.1: triethylamine / dichloromethane / 0.5 h / |Inert atmosphere; |Cooling 2.2: -3 - 20 °C / |Inert atmosphere 3.1: N,N-dimethyl-formamide / 100 °C / |Inert atmosphere 4.1: water; sodium hydroxide / ethanol / |Inert atmosphere; |Reflux 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / |Inert atmosphere; |Reflux View Scheme

1.1: triethylamine / dichloromethane / 0.5 h / |Inert atmosphere; |Cooling 1.2: -3 - 20 °C / |Inert atmosphere 2.1: N,N-dimethyl-formamide / 100 °C / |Inert atmosphere 3.1: water; sodium hydroxide / ethanol / |Inert atmosphere; |Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / |Inert atmosphere; |Reflux View Scheme

1: N,N-dimethyl-formamide / 100 °C / |Inert atmosphere 2: water; sodium hydroxide / ethanol / |Inert atmosphere; |Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / |Inert atmosphere; |Reflux View Scheme

1: water; sodium hydroxide / ethanol / |Inert atmosphere; |Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / |Inert atmosphere; |Reflux View Scheme

lithium aluminium tetrahydride

hydrogen bromide in sulfuric acid 20 h; Heating;

1: 80 percent / 47percent aq. HBr / H2SO4 / 20 h / Heating 2: 66 percent / NaOH, tetraethyleneglycol / 180 °C View Scheme