manganese(IV) oxide in pentane

sulfuric acid in acetone T=70°C; 1 h;

1: 1-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene / tetrahydrofuran / Heating 2: aq. HCl / tetrahydrofuran View Scheme

1: 64 percent / H2 / 5percent Pd-BaSO4 / ethyl acetate / 3 h 2: 25 percent / H2SO4 / acetone / 1 h / 70 °C View Scheme

chromium(VI) oxide; sulfuric acid

1: 60 percent / benzene / 12 h / Heating 2: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 3: 76 percent / LAH, EtOH / diethyl ether 4: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 5: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 6: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 7: 70 percent / LAH, EtOH / diethyl ether 8: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 2: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 3: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 4: 70 percent / LAH, EtOH / diethyl ether 5: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 77 percent / PBr3, pyridine / diethyl ether / Ambient temperature 2: 60 percent / benzene / 12 h / Heating 3: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 4: 76 percent / LAH, EtOH / diethyl ether 5: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 6: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 7: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 8: 70 percent / LAH, EtOH / diethyl ether 9: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 65 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 160 °C 2: 76 percent / LAH, EtOH / diethyl ether 3: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 4: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 5: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 6: 70 percent / LAH, EtOH / diethyl ether 7: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme

1: 76 percent / LAH, EtOH / diethyl ether 2: 80 percent / H2, quinoline / Lindlar's catalyst / hexane 3: 58 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h 4: 1.) NAOH / 1.) THF, < 20 deg C, 2a.) r. t., 5h, 2b.) 60 deg C, 4 h 5: 70 percent / LAH, EtOH / diethyl ether 6: 52 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 4 h View Scheme