1: iron dust, 12 M HCl / methanol / 10 h / Heating 2: Na2CO3 / diethyl ether; H2O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h 3: 93 percent / Jones reagent / acetone / 1.) 0 deg C, 30 min; 2.) room temp., 1 h 4: tetrahydrofuran / 2 h / Ambient temperature 5: 2 M aq. NaN3 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: toluene / 0.5 h / Heating 7: toluene / 2 h / 60 °C 8: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h 9: acetonitrile / 1 h 10: NaBH3CN / acetonitrile / 12 h / 50 °C 11: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 12: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 13: 5 M KOH / methanol / 3 h / Ambient temperature 14: DCC / tetrahydrofuran 15: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 16: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 17: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 18: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

sulfuric acid; nitric acid

1: iron dust, 12 M HCl / methanol / 10 h / Heating 2: Na2CO3 / diethyl ether; H2O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h 3: 77 percent / NaH / dimethylformamide / 3 h / Ambient temperature 4: 89 percent / Jones reagent / acetone / 2 h / Ambient temperature 5: tetrahydrofuran / 2 h / Ambient temperature 6: 5 M aq. NaN3 / H2O / 2 h / Ambient temperature 7: toluene / 1 h / Heating 8: toluene / 2 h / 60 °C 9: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h / Ambient temperature 10: 87 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 11: 80 percent / NaBH3CN / acetic acid / 0.5 h / Ambient temperature 12: 69 percent / NCS / CH2Cl2 / 0.25 h / 0 °C 13: 66 percent / DDQ / CH2Cl2 / 0.08 h 14: 60percent HClO4 / acetic acid / 0.5 h / Ambient temperature 15: 5 M NaOH / methanol / 1 h / Ambient temperature 16: DCC / tetrahydrofuran / 0 °C 17: 80 percent / BH3*SMe2 / tetrahydrofuran / 2 h / Ambient temperature 18: 64 percent / CAN / acetone; H2O / 0.08 h 19: 64 percent / NH4Cl / ethanol / 14 h / Ambient temperature View Scheme

1: 35 percent / aq. NaOH / ethanol / 3 h 2: 1.) NaBH4, 2.) H2 / 2.) Pd-C / 1.) MeOH, room temp., 4 h, 2.) 5 h 3: 1.) P2O5, 2.) H2 / 2.) Pd-C / 1.) benzene, reflux, 24 h, 2.) MeOH, 4 h 4: 2 h / 165 - 170 °C View Scheme

1: 35 percent / aq. NaOH / ethanol / 3 h 2: 1.) NaBH4, 2.) H2 / 2.) Pd-C / 1.) MeOH, room temp., 4 h, 2.) 5 h 3: 1.) P2O5, 2.) H2 / 2.) Pd-C / 1.) benzene, reflux, 24 h, 2.) MeOH, 4 h View Scheme

1: 69 percent / CrO3; H2SO4 / acetone; H2O / 24 h 2: 88 percent / phosphorus pentachloride / CH2Cl2 3: 86 percent / triethylamine / ethanol; ethyl acetate View Scheme

chromium(VI) oxide; sulfuric acid in water; acetone 24 h;

1: 90 percent / NaBH4 / tetrahydrofuran / 1 h / 40 - 60 °C 2: 93 percent / conc. HCl / 0.67 h / Heating 3: 85 percent / t-BuOK / dimethylformamide / 2 h / 120 °C 4: 99percent hydrazine hydrate / 5percent Ru/C / aq. ethanol / 24 h / Heating View Scheme

1: 90 percent / NaBH4 / tetrahydrofuran / 1 h / 40 - 60 °C 2: 93 percent / conc. HCl / 0.67 h / Heating 3: 85 percent / t-BuOK / dimethylformamide / 2 h / 120 °C 4: 99percent hydrazine hydrate / 5percent Ru/C / aq. ethanol / 24 h / Heating 6: 85 percent / 48percent aq. HBr / 2 h / Heating View Scheme

1: NaBH4 / tetrahydrofuran 2: aq. HCl 3: NaOEt 4: H2 / Pd-C / acetic acid 5: (i) NaNO2, aq. HCl, (ii) aq. HBF4 6: (i) (pyrolysis), (ii) H2, aq. HBr View Scheme