perchloric acid in tetrahydrofuran T=0°C; 1 h;

in dimethyl sulfoxide T=60 - 70°C; 7 h;

1: pyridine / 2 h / 0 °C 2: 40 mg / dimethylsulfoxide / 7 h / 60 °C 3: 96 percent / 1.5 M aq. perchloric acid / tetrahydrofuran / 1 h / 0 °C View Scheme

1: 1N NaOH / 1 h / 0 °C 2: thionyl chloride / benzene 3: diethyl ether / 3 h / 0 °C 4: aq. NaHCO3 / methanol 5: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 6: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 7: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 8: pyridine / 3 h / 0 °C 9: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 2: pyridine / 3 h / 0 °C 3: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 2: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 3: pyridine / 3 h / 0 °C 4: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: diethyl ether / 3 h / 0 °C 2: aq. NaHCO3 / methanol 3: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 4: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 5: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 6: pyridine / 3 h / 0 °C 7: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 2: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 3: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 4: pyridine / 3 h / 0 °C 5: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: pyridine / 3 h / 0 °C 2: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: diethyl ether / 1 h / 0 °C 2: 1.) methanesulfonyl chloride / 1.) pyridine, 1 h, 2.) dimethyl sulfoxide, 50-60 deg C, 1 h View Scheme