jones reagent

calcium carbonate; mercury dichloride in water; acetonitrile T=50°C; 1 h;

hydrogenchloride T=100 - 110°C; 13 h;

1: sec-BuLi / tetrahydrofuran / -78 °C 2: camphorsulfonic acid / acetonitrile / Heating View Scheme

1: LiAlH4 2: sec-BuLi / tetrahydrofuran / -78 °C 3: camphorsulfonic acid / acetonitrile / Heating View Scheme

1: 1.) NaBH4, 2.) trifluoroacetic acid / 1.) MeOH, 0 deg C, 2.) reflux 2: LiAlH4 3: sec-BuLi / tetrahydrofuran / -78 °C 4: camphorsulfonic acid / acetonitrile / Heating View Scheme

1: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h 2: 84 percent / chromium trioxide, periodic acid / H2O; acetone / 4 h / Ambient temperature 3: 1.) triethylamine, ethyl chloroformate, 2.) NH3 gas / 1.) CH2Cl2, -15 - -5 deg C, 1 h, 2.) -15 deg C - room temperature, 0.5 h 4: 62 percent / trifluoroacetic acid / CH2Cl2 / 4 h 5: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 6: 82 percent / acetic acid / 1 h 7: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 8: 54 percent / toluene / 2 h / 370 °C 9: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 10: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 11: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 56 percent / triethylamine / CH2Cl2 / 6 h / Heating 2: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h 3: 84 percent / chromium trioxide, periodic acid / H2O; acetone / 4 h / Ambient temperature 4: 1.) triethylamine, ethyl chloroformate, 2.) NH3 gas / 1.) CH2Cl2, -15 - -5 deg C, 1 h, 2.) -15 deg C - room temperature, 0.5 h 5: 62 percent / trifluoroacetic acid / CH2Cl2 / 4 h 6: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 7: 82 percent / acetic acid / 1 h 8: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 9: 54 percent / toluene / 2 h / 370 °C 10: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 11: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 12: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 84 percent / chromium trioxide, periodic acid / H2O; acetone / 4 h / Ambient temperature 2: 1.) triethylamine, ethyl chloroformate, 2.) NH3 gas / 1.) CH2Cl2, -15 - -5 deg C, 1 h, 2.) -15 deg C - room temperature, 0.5 h 3: 62 percent / trifluoroacetic acid / CH2Cl2 / 4 h 4: 90 percent / sodium borohydride, CeCl3 / methanol / 0.02 h 5: 82 percent / acetic acid / 1 h 6: 96 percent / hexamethyldisilazane / pyridine / 0.08 h 7: 54 percent / toluene / 2 h / 370 °C 8: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 9: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 10: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme

1: 96 percent / aq. HCl / tetrahydrofuran / 0.08 h 2: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / Ambient temperature 3: 62 percent / trifluoroacetic acid, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C View Scheme