trifluoroacetic acid in butan-1-ol 0.166667 h; Ambient temperature;

1: 1.) hexamethylphosphoramide (HMPA), n-butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.) 90 min 2: 90 percent / trifluoroacetic acid / butan-1-ol / 0.17 h / Ambient temperature View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 6: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 6: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 7: 55 percent / aq. NaOH / Ambient temperature View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating 6: 31 percent / 1.) triphenylphosphine, palladium(II) acetate, triethylamine / dioxane / 1 h / Heating 7: 55 percent / aq. NaOH / Ambient temperature 8: 51 percent / N-bromsuccinimide, potassium carbonate / dimethylformamide / 0.5 h / Ambient temperature View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h 5: 97 percent / iodine, nitric acid / dioxane / 3 h / Heating View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 1.) red mercuric oxide, mercuric chloride, 2.) sodium borohydride / 1.) aq. THF, RT 90 min, 2.) ethanol, water, RT, 30 min 3: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h 4: 66 percent / nitric acid, iodine / dioxane / 3 h / Heating View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 58 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h View Scheme

1: 62 percent / triethylamine, 4-dimethylaminopyridine (DMAP) / dimethylformamide / Ambient temperature 2: 85 percent / red mercuric oxide, mercuric chloride / tetrahydrofuran; H2O / 0.08 h / 0 °C 3: 70 percent / sodium borohydride / ethanol; H2O / 0.5 h / Ambient temperature 4: 81 percent / pyridine / 3.5 h / 103 °C 5: 98.5 percent / 4-dimethylaminopyridine (DMAP) / acetonitrile / Ambient temperature 6: 27 percent / α,α-azobis(isobutyronitrile) (AIBN), tributyltin hydride / toluene / 3 h / 75 - 80 °C 7: 61 percent / dichloroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature 8: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran 9: 46 percent / iodine, nitric acid / dioxane / 3 h / Heating View Scheme