1: 85 percent / pyridine / 0 °C 2: 81.3 percent / N-bromoacetamide, AcOH / acetone; H2O / 1 h View Scheme

1: 80.4 percent / pyridine / 1 h / 0 °C 2: 80.6 percent / Jones' reagent / acetone / 0.17 h / Ambient temperature View Scheme

potassium hydroxide in methanol; water 0.0666667 h; microwave irradiation;

1: 100 percent / 20 h / 60 °C / 8 Torr / Candida antarctica lipase immobilized on Florisil with Triton X-100 2: 91 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 1 h / 0 °C 3: 100 percent / Na2Cr2O7, H2SO4 / diethyl ether / Ambient temperature 4: 1) aq. NaOH, hydrazine hydrate / 1) diethylene glycol, 100 deg C, 2 h, 2) CH2Cl2, ether View Scheme

potassium hydroxide; triethylamine in dichloromethane; water; benzene

1.1: 4-(N,N-dimethlyamino)pyridine / toluene / 20 °C / |Large scale 1.2: 19 h / 20 °C / |Large scale 2.1: acetic acid; sodium hypochlorite / ethyl acetate / 30 - 40 °C / |Large scale 3.1: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 4 h / 120 - 210 °C / |Large scale 4.1: sulfuric acid; sodium bromide; Sodium bromate; water / butan-1-ol; dichloromethane / 0 - 55 °C / |Large scale 5.1: sodium / Sec-butyl alcohol / 0.5 h / |Reflux; |Large scale 5.2: 30 °C / |Large scale 5.3: |Large scale 6.1: water; phosphoric acid / Sec-butyl alcohol / 70 °C / |Large scale 6.2: 2 h / |Reflux; |Large scale View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine / toluene / 20 °C / |Large scale 1.2: 19 h / 20 °C / |Large scale 2.1: acetic acid; sodium hypochlorite / ethyl acetate / 30 - 40 °C / |Large scale 3.1: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 4 h / 120 - 210 °C / |Large scale 4.1: sulfuric acid; sodium bromide; Sodium bromate; water / butan-1-ol; dichloromethane / 0 - 55 °C / |Large scale 5.1: sodium / Sec-butyl alcohol / 0.5 h / |Reflux; |Large scale 5.2: 30 °C / |Large scale 5.3: |Large scale 6.1: water; phosphoric acid / Sec-butyl alcohol / 70 °C / |Large scale 6.2: 2 h / |Reflux; |Large scale 7.1: water; sodium hydroxide / 2 h / 97 °C / |Large scale View Scheme

1: 86 percent / 60percent perchloric acid / 1.5 h / 50 °C 2: 100 percent / ammonia / methanol / 0.5 h / Ambient temperature 3: 70 percent / iodoxybenzene, benzeneseleninic anhydride / toluene / 3 h / Heating 4: 87 percent / 2 M LiOH / methanol / 1.5 h / Ambient temperature 5: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 6: H+ View Scheme

1: N-bromosuccinmide / water; acetone / 72 h / 20 °C 2: pyridine / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 20 °C 3: bromine; acetic acid / 48 h / 20 °C 4: potassium hydroxide / methanol / 20 °C 5: toluene-4-sulfonic acid / 20 °C 6: zinc(II) chloride; sodium tetrahydroborate / diethyl ether View Scheme

1: 86 percent / 60percent perchloric acid / 1.5 h / 50 °C 2: 100 percent / ammonia / methanol / 0.5 h / Ambient temperature 3: 70 percent / iodoxybenzene, benzeneseleninic anhydride / toluene / 3 h / Heating 4: 87 percent / 2 M LiOH / methanol / 1.5 h / Ambient temperature 5: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 6: H+ 7: 88 percent / K-Selectride / tetrahydrofuran / 3 h / -20 °C 8: 100 percent / methanolic KOH View Scheme