palladium on activated charcoal; hydrogen in methanol; acetic acid P=760 Torr; 2.5 h;

1: H2, Pd-C / methanol; acetic acid / 2.5 h / 760 Torr 2: 89.3 percent / diethyl ether / 21 h / Irradiation View Scheme

1: H2, Pd-C / methanol; acetic acid / 2.5 h / 760 Torr 2: 2.) H2 / 1.) MgSO4, 2.) PtO2 / 1.) EtOAC, room temp, 1.5 h, 2.) C2H5OH, 6.5 h 3: 34 percent / methanol / 1.33 h / Irradiation View Scheme

1: H2, Pd-C / methanol; acetic acid / 2.5 h / 760 Torr 2: 89.3 percent / diethyl ether / 21 h / Irradiation 3: LiAlH4 / tetrahydrofuran / 4 h / Heating 4: 92 percent / NaHCO3 / CH2Cl2; H2O / 1 h View Scheme

1: H2, Pd-C / methanol; acetic acid / 2.5 h / 760 Torr 2: 89.3 percent / diethyl ether / 21 h / Irradiation 3: 77 percent / (C2H5)3N / tetrahydrofuran / 1.) room temp, 0.5 h, 2.) reflux, 0.5 h View Scheme