lithium aluminium tetrahydride in tetrahydrofuran 1 h; Ambient temperature;

1: 1.) LDA / 1.) THF, -78 degC, 35 min; 2.) THF, -78 degC, 1.5 h 2: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 3: 1.) n-BuLi 4: 28 percent / Raney-Ni / ethanol / 12 h / Heating 5: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 87 percent / 18-crown-6 / H2O; ethyl acetate / 14 h / 50 °C 2: 1.) n-BuLi 3: 28 percent / Raney-Ni / ethanol / 12 h / Heating 4: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, -78 degC, 3 h; 2.) THF, -78 degC, 0.5 h, allowed to warm to room temp. for 15 h 2: 57 percent / Raney-Ni / ethanol / 6 h / Heating 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, -78 degC, 3 h; 2.) THF, -78 degC, 0.5 h, allowed to warm to room temp. for 15 h 2: 57 percent / Raney-Ni / ethanol / 6 h / Heating 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1.) n-BuLi 2: 28 percent / Raney-Ni / ethanol / 12 h / Heating 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 2.) conc. HCl / 1.) CHCl3, room temp., 2 h; 2.) room temp., 2 h 2: 1.) n-BuLi / 1.) THF, -78 degC, 3 h; 2.) THF, -78 degC, 0.5 h, allowed to warm to room temp. for 15 h 3: 57 percent / Raney-Ni / ethanol / 6 h / Heating 4: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1.) LDA, HMPA / 1.) THF, -78 degC, 1 h; 2.) THF, -78 degC, 4 h, room temp., 18 h 2: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 65 percent / Raney-Ni / ethanol / 5 h / Heating 2: 1.) LDA, HMPA / 1.) THF, -78 degC, 1 h; 2.) THF, -78 degC, 4 h, room temp., 18 h 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1.) LDA / 1.) THF, HMPA, -78degC, 0.5 h; 2.) -78 degC, 1 h, -20 degC, 4 h, room temp., 19 h 2: 85 percent / methanol; H2O / 0.5 h / Ambient temperature 3: 1.) n-BuLi / 1.) THF, -78 degC, 3 h; 2.) THF, -78 degC, 0.5 h, allowed to warm to room temp. for 15 h 4: 57 percent / Raney-Ni / ethanol / 6 h / Heating 5: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature View Scheme