in diethyl ether

sodium tetrahydroborate in ethanol; water Ambient temperature;

1: 65 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: 59 percent / NaNH2 / tetrahydrofuran / 1.5 h / 5 - 22 °C 3: 66 percent / H2, (η6-PhCO2Me)Cr(CO)3 / acetone / 2 h / 120 - 125 °C / 60800 Torr 4: NaBH4 / ethanol; H2O / Ambient temperature View Scheme

1: 59 percent / NaNH2 / tetrahydrofuran / 1.5 h / 5 - 22 °C 2: 66 percent / H2, (η6-PhCO2Me)Cr(CO)3 / acetone / 2 h / 120 - 125 °C / 60800 Torr 3: NaBH4 / ethanol; H2O / Ambient temperature View Scheme

potassium hydroxide 0.5 h; Ambient temperature; Yield given;

1: aq. KOH / 0.5 h / Ambient temperature 2: 1.) 2,2'-dipyridyl disulfide, PPh3, 2.) AgClO4 / 1.) CH3CN, from 20 deg C to 25 deg C, 2 h, 2.) CH3CN, p-xylene, reflux, 6 h View Scheme