manganese(IV) oxide in chloroform 1 h;

hydrogenchloride; n-butyllithium 1.) THF, -70 deg C, 10 min; -70 to 0 deg C, 2.) EtOH, reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

hydrogen; ammonium formate; palladium on activated charcoal in methanol Heating;

1: 83 percent / NaH / dimethylformamide / 3 h / 100 °C 2: 97 percent / NaBH4 / methanol / 0.33 h / Ambient temperature 3: 98 percent / SOCl2 / 1.) 0 deg C, 30 min, 2.) RT, 30 min 4: 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 5: 84 percent / 0.25 N aq. HCl / methanol / 1.5 h / Ambient temperature 6: 86 percent / 6 N aq. HCl / 1 h / Heating 7: 83 percent / H2O / Raney Ni / ethanol / 8 h / Heating View Scheme

1: 73 percent / NaH / dimethylformamide / 1 h / 110 °C 2: 100 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in toluene Heating;