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

1: 97 percent / Et3N / CH2Cl2 / -20 °C 2: 87 percent / K3PO4 / Pd(PPh3)4 / dioxane / 80 °C 3: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

1: 94 percent / Claycop; Ac2O / diethyl ether / 1 h / 20 °C 2: 96 percent / AlCl3 / CH2Cl2 / 21 h / 20 °C 3: 97 percent / Et3N / CH2Cl2 / -20 °C 4: 87 percent / K3PO4 / Pd(PPh3)4 / dioxane / 80 °C 5: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

1: 96 percent / AlCl3 / CH2Cl2 / 21 h / 20 °C 2: 97 percent / Et3N / CH2Cl2 / -20 °C 3: 87 percent / K3PO4 / Pd(PPh3)4 / dioxane / 80 °C 4: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

1: 87 percent / K3PO4 / Pd(PPh3)4 / dioxane / 80 °C 2: 100 percent / H2 / Pd/C / methanol / 20 °C View Scheme

1: 30 percent / 96 h / 130 °C 2: 86 percent / lithium aluminum hydride / diethyl ether / 2 h / Heating 3: 97 percent / phosphorus tribromide / CH2Cl2 / 4 h / Heating 4: 79 percent / lithium aluminum hydride / toluene / 0.5 h / Heating 5: 43 percent / conc. HNO3; conc. H2SO4 / CH2Cl2 / 1 h / 20 °C 6: 88 percent / H2 / Pd/C / methanol / 800 - 900 Torr View Scheme