potassium hydroxide in ethanol 1.5 h; Heating;

2: aq. 4M KOH / H2O; ethanol / 5 h / Heating View Scheme

1.1: mercury dichloride / 18 h / 150 °C / Reflux; Inert atmosphere 2.1: ethanol; sodium / 3 h / Inert atmosphere; Reflux 3.1: potassium hydroxide / ethanol; water / 0.75 h / Inert atmosphere; Reflux 3.2: pH 2 - 3 / Inert atmosphere View Scheme

1: 83 percent / 1. 150 deg C, 1 h, 4.0E3 Pa; 2. 165 deg C, 2.5 h; 3. 180 deg C, 2.5 h 2: 81 percent / H2SO4 / CHCl3 / 16 h / Heating 3: 85 percent / H2 / PtO2 / methanol / 7 h View Scheme

1: 83 percent / 1. 150 deg C, 1 h, 4.0E3 Pa; 2. 165 deg C, 2.5 h; 3. 180 deg C, 2.5 h 2: 81 percent / H2SO4 / CHCl3 / 16 h / Heating 3: 85 percent / H2 / PtO2 / methanol / 7 h 4: 88 percent / pyridine / 336 h 5: 80 percent / NH4Br, NH3 / 144 h / Ambient temperature 6: 59 percent / NaN3 / methanol; H2O / 20 h / Heating 7: 81 percent / H2 / PtO2 / methanol / 6 h / Ambient temperature 8: 79 percent / HCl / H2O / 20 h / Heating View Scheme

1: 83 percent / 1. 150 deg C, 1 h, 4.0E3 Pa; 2. 165 deg C, 2.5 h; 3. 180 deg C, 2.5 h 2: 81 percent / H2SO4 / CHCl3 / 16 h / Heating 3: 85 percent / H2 / PtO2 / methanol / 7 h 4: 88 percent / pyridine / 336 h 5: 1. NH4Br, NH3; 2. HCl / 1. 88 deg C, 16 h; 2. H2O, 88 deg C, 20 h, heating View Scheme

1: 83 percent / 1. 150 deg C, 1 h, 4.0E3 Pa; 2. 165 deg C, 2.5 h; 3. 180 deg C, 2.5 h 2: 81 percent / H2SO4 / CHCl3 / 16 h / Heating 3: 85 percent / H2 / PtO2 / methanol / 7 h 4: 88 percent / pyridine / 336 h 5: 1. NH4Br, NH3; 2. HCl / 1. 88 deg C, 16 h; 2. H2O, 88 deg C, 20 h, heating View Scheme

1.1: pyridine / 12 h / 120 °C 2.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 7 h / 80 °C / Inert atmosphere 2.2: 1 h / 0 - 20 °C / Inert atmosphere View Scheme

pyridine T=120°C; 12 h;

1: 88.6 percent / 215 °C / 0.4 Torr 2: 99.5 percent / oxalyl chloride / CCl4 / 1) 0 deg C, 1 h, 2) r.t., 12 h 3: CCl4 / 5 h / Ambient temperature 4: 91.9 percent / LiAlH4 / 1,2-dimethoxy-ethane / 60 h / 85 °C 5: 81.2 percent / imidazole / dimethylformamide / 20 h / Ambient temperature 6: 99.2 percent / H2 / Pd/C / 1,2-dimethoxy-ethane / 8 h / 760 Torr / Ambient temperature 7: 76.2 percent / Et3N / CH2Cl2 / 15 h / Ambient temperature 8: 46.9 percent / DBU / dimethylsulfoxide / 35 h / 80 °C 9: 60 mg / aq. HF-urea / tetrahydrofuran / 15 h / Ambient temperature View Scheme