1: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 2: 16 percent / H2, sodium acetate / 10 percent Pd/C / benzene; methanol / 40 °C View Scheme

1: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 2: 1) sodium acetate, H2; 2) 4-(dimethylamino)pyridine, triethyl amine / 1) 10 percent Pd/C / 1) benzene, CH3OH, 40 deg C; 2) 15 h at room temp. 3: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile View Scheme

1: 70 percent / 4-(dimethylamino)pyridine, triethylamine / 15 h / Ambient temperature 2: 1) sodium acetate, H2; 2) 4-(dimethylamino)pyridine, triethyl amine / 1) 10 percent Pd/C / 1) benzene, CH3OH, 40 deg C; 2) 15 h at room temp. 3: 65 percent / 10 percent ammonium cer(IV) nitrate (aq.) / acetonitrile 4: 70 percent / conc. H2SO4 / 0.08 h View Scheme