lithium aluminium tetrahydride in 1,4-dioxane T=80°C;

in tetrahydrofuran; pentane T=-40°C;

lithium aluminium tetrahydride in tetrahydrofuran 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h;

1: 1.) BuLi, Me3Al / 1.) hexane, 0 deg C, 10 min, 2.) hexane, 60 deg C, 1 h 45 min 2: 90 percent / H2 / (Ph3P)3RhCl / benzene; ethanol / 16 h / 760 Torr / Ambient temperature 3: 85 percent / ZnCl2 / 1.) -10 deg C, 30 min, 2.) 0 deg C, 20 min 4: 94 percent / pyridine / 1.) 0 deg C, 15 min, 2.) room temperature, 70 min 5: 93 percent / LiAlH4 / tetrahydrofuran / 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h View Scheme

1: 90 percent / H2 / (Ph3P)3RhCl / benzene; ethanol / 16 h / 760 Torr / Ambient temperature 2: 85 percent / ZnCl2 / 1.) -10 deg C, 30 min, 2.) 0 deg C, 20 min 3: 94 percent / pyridine / 1.) 0 deg C, 15 min, 2.) room temperature, 70 min 4: 93 percent / LiAlH4 / tetrahydrofuran / 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h View Scheme

1: 94 percent / pyridine / 1.) 0 deg C, 15 min, 2.) room temperature, 70 min 2: 93 percent / LiAlH4 / tetrahydrofuran / 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h View Scheme

1: 85 percent / ZnCl2 / 1.) -10 deg C, 30 min, 2.) 0 deg C, 20 min 2: 94 percent / pyridine / 1.) 0 deg C, 15 min, 2.) room temperature, 70 min 3: 93 percent / LiAlH4 / tetrahydrofuran / 1.) -70 deg C, 10 min, 2.) without cooling, 1 h, 3.) 50 deg C, 3 h View Scheme

lithium aluminium tetrahydride; cryptand tris(3,6-dioxaheptyl)amine 1.) ether, 24 h, reflux; 2.) ether, rt., 1 day; Yield given. Multistep reaction;

1: 68 percent / toluene / 0.25 h / 0 °C 2: pentane / 1.) -50 deg C, 30 min, 2.) to r.t. View Scheme

in pentane 1.) -50 deg C, 30 min, 2.) to r.t.;