iron(III) chloride in benzene 0.25 h;

1: 89 percent / H2 / 5percent Pd/BaSO4 / pyridine 2: 82 percent / pyridine / CHCl3 / 6 h / 0 °C 3: 100 percent / NaI / acetone / 48 h / 25 °C 4: 96 percent / acetonitrile / 48 h / Heating 5: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 6: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 7: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme

2: 95 percent / H2SO4 / 16 h / Heating 3: 100 percent / LiAlH4 / diethyl ether / 3 h / 25 °C 4: 100 percent / pyridine / toluene / 3 h / Heating 5: 90 percent / CrO3 / acetic acid; H2O / 1.5 h 6: 91 percent / H2SO4 / 12 h / 25 °C 7: 77 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h 8: 100 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h 9: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 10: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 11: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme

1: pyridinium toluene-p-sulphonate / methanol / 18 h / 55 °C 2: 89 percent / H2 / palladized barium sulphate (5percent) / pyridine / 2 h 3: 82 percent / pyridine / CHCl3 / 6 h / 0 °C 4: 100 percent / sodium iodide / acetone / 48 h / Ambient temperature 5: 93 percent / acetonitrile / 48 h / 80 °C 6: 1) butyl-lithium, 2) hexamethylphosphoric triamide / hexane, THF, 1) - 78 deg C, 0.5 h, 2) - 78 deg C, 2 h 7: 100 percent / LiAlH4 / tetrahydrofuran / 0.25 h 8: 100 percent / 1percent aq. iron(III)chloride / benzene / 0.25 h View Scheme

1: H2 / palladized charcoal (10percent) / ethyl acetate 2: 92 percent / conc. sulphuric acid / 16 h / Heating 3: 100 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature 4: 100 percent / pyridine / toluene / 3 h / 60 °C 5: 90 percent / chromium trioxide / H2O; acetic acid / 1) 0 deg C, 0.5 h, 2) r.t., 1 h 6: 91 percent / conc. sulphuric acid / 12 h / Ambient temperature 7: 77 percent / H2 / palladized charcoal (10percent) / ethyl acetate 8: 100 percent / pyridinium chlorochromate, anhydrous sodium acetate / CH2Cl2 / 3 h / Ambient temperature 9: 1) butyl-lithium, 2) hexamethylphosphoric triamide / hexane, THF, 1) - 78 deg C, 0.5 h, 2) - 78 deg C, 2 h 10: 100 percent / LiAlH4 / tetrahydrofuran / 0.25 h 11: 100 percent / 1percent aq. iron(III)chloride / benzene / 0.25 h View Scheme

1: water, NaOH / methanol / 5 h / Heating 2: H2 / palladized charcoal (10percent) / ethyl acetate 3: 92 percent / conc. sulphuric acid / 16 h / Heating 4: 100 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature 5: 100 percent / pyridine / toluene / 3 h / 60 °C 6: 90 percent / chromium trioxide / H2O; acetic acid / 1) 0 deg C, 0.5 h, 2) r.t., 1 h 7: 91 percent / conc. sulphuric acid / 12 h / Ambient temperature 8: 77 percent / H2 / palladized charcoal (10percent) / ethyl acetate 9: 100 percent / pyridinium chlorochromate, anhydrous sodium acetate / CH2Cl2 / 3 h / Ambient temperature 10: 1) butyl-lithium, 2) hexamethylphosphoric triamide / hexane, THF, 1) - 78 deg C, 0.5 h, 2) - 78 deg C, 2 h 11: 100 percent / LiAlH4 / tetrahydrofuran / 0.25 h 12: 100 percent / 1percent aq. iron(III)chloride / benzene / 0.25 h View Scheme

1: 96 percent / acetonitrile / 48 h / Heating 2: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 3: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 4: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme

1: 82 percent / pyridine / CHCl3 / 6 h / 0 °C 2: 100 percent / NaI / acetone / 48 h / 25 °C 3: 96 percent / acetonitrile / 48 h / Heating 4: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 5: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 6: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme

1: 100 percent / NaI / acetone / 48 h / 25 °C 2: 96 percent / acetonitrile / 48 h / Heating 3: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 4: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 5: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme

1: 100 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h 2: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 3: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 4: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme