hydrogen; palladium on activated charcoal in ethanol P=2942.03 Torr; 24 h; Ambient temperature;

1: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 3: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 4: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 5: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme