hydrogen; palladium on activated charcoal in methanol P=760 Torr; 0.5 h; Ambient temperature;

1: 96 percent / active γ-MnO2 / CHCl3 / 1 h / Heating 2: 83 percent / NaH / dimethylformamide / 3 h / 100 °C 3: 97 percent / NaBH4 / methanol / 0.33 h / Ambient temperature 4: 98 percent / SOCl2 / 1.) 0 deg C, 30 min, 2.) RT, 30 min 5: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 10 min, 2.)a) hexane, THF, -78 deg C, 1 h, b) -50 deg C, 20 h 6: 84 percent / 0.25 N aq. HCl / methanol / 1.5 h / Ambient temperature 7: 86 percent / 6 N aq. HCl / 1 h / Heating 8: 83 percent / H2O / Raney Ni / ethanol / 8 h / Heating View Scheme

manganese(IV) oxide in chloroform 1 h;

1: 96 percent / active γ-MnO2 / CHCl3 / 1 h / Heating 2: 73 percent / NaH / dimethylformamide / 1 h / 110 °C 3: 100 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme