1: 1.) KOH / 1.) DMSO, 10 min, 2.) DMSO, 2 h 2: 3.7 g / H2 / Pd/C / methanol / 1 h / Ambient temperature 3: 95.1 percent / H2 / Ru/C / methanol / 15 h / 50 °C / 2250.2 Torr 4: 49.8 percent / Jones reagent / acetone / 10 h View Scheme

1: 1.) KOH / 1.) DMSO, 10 min, 2.) DMSO, 2 h 2: 3.7 g / H2 / Pd/C / methanol / 1 h / Ambient temperature View Scheme

1: 1.) KOH / 1.) DMSO, 10 min, 2.) DMSO, 2 h 2: 3.7 g / H2 / Pd/C / methanol / 1 h / Ambient temperature 3: 95.1 percent / H2 / Ru/C / methanol / 15 h / 50 °C / 2250.2 Torr 4: 49.8 percent / Jones reagent / acetone / 10 h 6: 55.1 percent / formic acid / 0.5 h / 80 °C View Scheme