1: 100 percent / H2 / palladium on carbon / ethanol / 12 h / 20 °C / 760 Torr 2: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 20 °C 3: 96 percent / sodium; naphthalene / tetrahydrofuran / 1 h / -78 °C 4: 87 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 18 h / 0 °C 5: 95 percent / trifluoroacetic acid; NaHCO3 / 2 h / 20 °C View Scheme