hydrogen; palladium on activated charcoal in dichloromethane T=25°C; P=3040 Torr; 96 h;

1: 97 percent / H2 / Pd/C / CH2Cl2 / 48 h / 20 °C / 38000 Torr 2: NaH / tetrahydrofuran / 72 h / 20 °C View Scheme

1: 97 percent / H2 / 10percent Pd/C / CH2Cl2 / 96 h / 25 °C / 3040 Torr 2: 95 percent / KOH / CH2Cl2 / 3 h / 0 °C 3: 1) NaH / 1) THF, 24 h, 2) 96 h 4: 97 percent / H2 / 10percent Pd/C / CH2Cl2 / 96 h / 25 °C / 3040 Torr View Scheme

1: 97 percent / H2 / Pd/C / CH2Cl2 / 48 h / 20 °C / 38000 Torr 2: 99 percent / Et3N; KOH / tetrahydrofuran; H2O View Scheme