ammonia T=40°C;

1: aq. 4M KOH / H2O; ethanol / 5 h / Heating 2: 88.6 percent / 215 °C / 0.4 Torr 3: 99.5 percent / oxalyl chloride / CCl4 / 1) 0 deg C, 1 h, 2) r.t., 12 h 4: CCl4 / 5 h / Ambient temperature 5: 91.9 percent / LiAlH4 / 1,2-dimethoxy-ethane / 60 h / 85 °C 6: 81.2 percent / imidazole / dimethylformamide / 20 h / Ambient temperature 7: 99.2 percent / H2 / Pd/C / 1,2-dimethoxy-ethane / 8 h / 760 Torr / Ambient temperature 8: 76.2 percent / Et3N / CH2Cl2 / 15 h / Ambient temperature 9: 46.9 percent / DBU / dimethylsulfoxide / 35 h / 80 °C 10: 60 mg / aq. HF-urea / tetrahydrofuran / 15 h / Ambient temperature View Scheme

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

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

1: CCl4 / 5 h / Ambient temperature 2: 91.9 percent / LiAlH4 / 1,2-dimethoxy-ethane / 60 h / 85 °C 3: 81.2 percent / imidazole / dimethylformamide / 20 h / Ambient temperature 4: 99.2 percent / H2 / Pd/C / 1,2-dimethoxy-ethane / 8 h / 760 Torr / Ambient temperature 5: 76.2 percent / Et3N / CH2Cl2 / 15 h / Ambient temperature 6: 46.9 percent / DBU / dimethylsulfoxide / 35 h / 80 °C 7: 60 mg / aq. HF-urea / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 81.2 percent / imidazole / dimethylformamide / 20 h / Ambient temperature 2: 99.2 percent / H2 / Pd/C / 1,2-dimethoxy-ethane / 8 h / 760 Torr / Ambient temperature 3: 76.2 percent / Et3N / CH2Cl2 / 15 h / Ambient temperature 4: 46.9 percent / DBU / dimethylsulfoxide / 35 h / 80 °C 5: 60 mg / aq. HF-urea / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 76.2 percent / Et3N / CH2Cl2 / 15 h / Ambient temperature 2: 46.9 percent / DBU / dimethylsulfoxide / 35 h / 80 °C 3: 60 mg / aq. HF-urea / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 46.9 percent / DBU / dimethylsulfoxide / 35 h / 80 °C 2: 60 mg / aq. HF-urea / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 31 percent / pyridine / 3 h / 50 °C 2: 85 percent / conc. HCl / ethanol; CHCl3 / 1 h / Ambient temperature 3: 78 percent / liq. NH3 / 40 °C View Scheme

1: 79 percent / LiAlH4 / diethyl ether / 2 h / Heating 2: 73 percent / NEt3 / butan-1-ol / Heating 3: 69 percent / conc. HCl / 6 h / Ambient temperature 4: 31 percent / pyridine / 3 h / 50 °C 5: 85 percent / conc. HCl / ethanol; CHCl3 / 1 h / Ambient temperature 6: 78 percent / liq. NH3 / 40 °C View Scheme