hydrogen; palladium on activated charcoal in methanol 16 h;

1: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h 2: 65 percent / tetraethylammonium bromide, molecular sieves / CH2Cl2; dimethylformamide / 16 h / Ambient temperature 3: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol View Scheme