sodium hydroxide 1.) water, 50 deg C; Yield given. Multistep reaction;

1: 1.) aq. NaOH / 1.) 50 deg C 2: 79 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 85 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme

1: sodium iodide / acetone / 1 h / Heating 2: 97 percent / acetonitrile / 36 h / Heating 3: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 10 min, 2.) THF, 0 deg C, 5 min 4: 70 percent / sodium borohydride / methanol / 0.08 h / 0 °C View Scheme

1: sodium iodide / acetone / 1 h / Heating 2: 97 percent / acetonitrile / 36 h / Heating 3: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 10 min, 2.) THF, 0 deg C, 5 min 4: 70 percent / sodium borohydride / methanol / 0.08 h / 0 °C 5: 100 percent / lithium hydroxide / propan-2-ol; H2O / 1.5 h / Ambient temperature View Scheme

lithium aluminium tetrahydride

1: 1.) NaH / 1.) DMF, 110 deg C, 30 min, 2.) DMF 2: LiOH*H2O, H2O / methanol / 0.5 h / Heating View Scheme

1: sodium iodide / acetone / 1 h / Heating 2: 97 percent / acetonitrile / 36 h / Heating 3: 1.) potassium tert-butoxide / 1.) THF, 0 deg C, 10 min, 2.) THF, 0 deg C, 5 min 4: 70 percent / sodium borohydride / methanol / 0.08 h / 0 °C View Scheme

sodium iodide in acetone 1 h; Heating; Yield given;

1: sodium iodide / acetone / 1 h / Heating 2: 97 percent / acetonitrile / 36 h / Heating View Scheme