1: H2 / Pd-C 2: Na2CO3 3: OH(1-) View Scheme

1: 89 percent / hydrogen / platinum oxide hydrate / aq. ethanol / 18 h / 1520 - 2280 Torr 2: potassium carbonate / acetone 3: 1.) lithium diisopropylamide / 1.) THF, -78 -> -60 deg C, 2.) ethanol, reflux; other reagent: sodium View Scheme

hydrogen; platinum(IV) oxide in ethanol 20 h; Ambient temperature;

1: 98 percent / hydrogen / PtO2 / aq. ethanol / 20 h / Ambient temperature 2: 91 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: DIBALH / CH2Cl2 / 0.5 h / -78 °C 4: 4 Angstroem molecular sieves / CH2Cl2 / 2.5 h / Ambient temperature 5: hydrogen / 1.) PtO2; 2.) Pd/C / 1.) aq. EtOH; 2.) aq. EtOH, 6 h View Scheme

1: 98 percent / hydrogen / PtO2 / aq. ethanol / 20 h / Ambient temperature 2: 91 percent / K2CO3 / dimethylformamide / 24 h / 80 °C 3: DIBALH / CH2Cl2 / 0.5 h / -78 °C View Scheme