sodium hydroxide in ethanol 1.5 h; Heating;

sodium hydroxide; potassium iodide; Tl(OCOCF3)3 1.) trifluoroacetic acid, 5 d, r.t.; 2.) water, 15 min; 3.) 2 h, reflux; Yield given. Multistep reaction;

trifluoroacetic acid; sodium iodide in acetone 1.)0-5 deg C, 2.)15 min., 25 deg C;

1: 95 percent / diethyl ether / 12 h / 0 °C 2: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 3: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

1: 90 h / 100 °C 2: SOCl2 / 14 h / Ambient temperature 3: 83 percent / SnCl4 / CH2Cl2 / 1.)0 deg C, 2.)R.T., 16 h 4: 90 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / Heating 5: 67 percent / Raney nickel, 10percent Na2CO3 / ethanol / 16 h / Heating 6: 96 percent / diethyl ether / 12 h / 0 °C 7: 1.)thallium(III) trifluoroacetate, trifluoracetic acid, 2.)isomayl nitrite, 12N HCl, AcOH / 1.)r.t., 48 h, 2.)CH2Cl2, red lights, 10 min. 8: 90 percent / NaBH4 / Palladium on charcoal / methanol / 0.5 h / Ambient temperature 9: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 10: 53 percent / 1N NaOH / ethanol / 1 h / Heating 11: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme

1: SOCl2 / 14 h / Ambient temperature 2: 83 percent / SnCl4 / CH2Cl2 / 1.)0 deg C, 2.)R.T., 16 h 3: 90 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / Heating 4: 67 percent / Raney nickel, 10percent Na2CO3 / ethanol / 16 h / Heating 5: 96 percent / diethyl ether / 12 h / 0 °C 6: 1.)thallium(III) trifluoroacetate, trifluoracetic acid, 2.)isomayl nitrite, 12N HCl, AcOH / 1.)r.t., 48 h, 2.)CH2Cl2, red lights, 10 min. 7: 90 percent / NaBH4 / Palladium on charcoal / methanol / 0.5 h / Ambient temperature 8: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 9: 53 percent / 1N NaOH / ethanol / 1 h / Heating 10: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme

1: 83 percent / SnCl4 / CH2Cl2 / 1.)0 deg C, 2.)R.T., 16 h 2: 90 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / Heating 3: 67 percent / Raney nickel, 10percent Na2CO3 / ethanol / 16 h / Heating 4: 96 percent / diethyl ether / 12 h / 0 °C 5: 1.)thallium(III) trifluoroacetate, trifluoracetic acid, 2.)isomayl nitrite, 12N HCl, AcOH / 1.)r.t., 48 h, 2.)CH2Cl2, red lights, 10 min. 6: 90 percent / NaBH4 / Palladium on charcoal / methanol / 0.5 h / Ambient temperature 7: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 8: 53 percent / 1N NaOH / ethanol / 1 h / Heating 9: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme

1: 90 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / Heating 2: 67 percent / Raney nickel, 10percent Na2CO3 / ethanol / 16 h / Heating 3: 96 percent / diethyl ether / 12 h / 0 °C 4: 1.)thallium(III) trifluoroacetate, trifluoracetic acid, 2.)isomayl nitrite, 12N HCl, AcOH / 1.)r.t., 48 h, 2.)CH2Cl2, red lights, 10 min. 5: 90 percent / NaBH4 / Palladium on charcoal / methanol / 0.5 h / Ambient temperature 6: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 7: 53 percent / 1N NaOH / ethanol / 1 h / Heating 8: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme

1: 90 percent / NaBH4 / Palladium on charcoal / methanol / 0.5 h / Ambient temperature 2: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 3: 53 percent / 1N NaOH / ethanol / 1 h / Heating 4: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme

1: SOCl2 / dimethylformamide / 1 h / 80 °C 2: AlCl3 / dimethylformamide / 1 h / 90 °C 3: 85 percent / dimethylsulfoxide / 2 h / 80 °C 4: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 5: 95 percent / diethyl ether / 12 h / 0 °C 6: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 7: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 8: 1.) n-BuLi / 1.) THF, -78 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 45 min 9: 89 percent / concd H2SO4 / 24 h / Heating 10: 95 percent / LiAlH4 / diethyl ether / 4 h / Heating 11: 85 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 12: 82 percent / dimethylsulfoxide / 2 h / 80 °C 13: 91 percent / KOH / ethane-1,2-diol / 6 h / Heating 14: 95 percent / diethyl ether / 12 h / 0 °C 15: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 16: 95 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme