hydrogen; palladium on activated charcoal in methanol T=20°C; 15 h;

pyridine; palladium hydroxide (20 on carbon); hydrogen in tetrahydrofuran; methanol T=20°C;

1.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C 2.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C 3.1: (NH4)2SO4 / 24 h / Heating 3.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating 3.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating View Scheme