sodium hydride; cesium fluoride in N,N-dimethyl-formamide T=70°C; 24 h;

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C 1.2: 70 °C 2.1: water; sodium carbonate / 55 °C View Scheme

1: 96 percent / conc. hydrobromic acid / acetic acid / 41 h / Heating 2: 96 percent / K2CO3 / acetone; dimethylformamide / 64 h / Ambient temperature 3: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C 4: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature 5: 69 percent / hydrogen / 84.5percent PtO2 / ethanol / 2.75 h / 2327.2 Torr 6: 111 g / pyridine / 1.42 h / 5 °C 7: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride 8: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C 9: 81 percent / hydrogen / 84.5percent PtO2 / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr 10: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h 11: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating 12: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene 13: 72 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 72 h / Ambient temperature 14: (dimethylamino)pyridine / pyridine / 0.17 h / Ambient temperature 15: 1.) trimethylsilyl chloride, NaI, 2.) triethylamine / 1.) acetonitrile, benzonitrile, 65 deg C, 45 min, reflux, 15 min View Scheme

1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 5: 70 percent aq. HClO4 / 1 h / 20 °C 6: H2O / 0.08 h / Heating View Scheme

potassium hydroxide in ethanol 5 h; Reflux;

1: 22 percent / sodium hydride; cesium fluoride / various solvent(s); dimethylformamide / 24 h / 70 °C 2: 76 percent / conc. sulfuric acid / H2O / 0.33 h / Heating View Scheme

1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C View Scheme

in ethanol T=120 - 130°C; 3 h;

1: 96 percent / Na2CO3 / ethanol; H2O / 5 h / Heating 2: Cl2; HOAc; H2O / 0.25 h / 5 °C 3: 88 percent / aq. NH3 / CH2Cl2 / 0.5 h / 5 °C View Scheme

1: 70 percent / dimethylformamide / Heating 2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 25 °C View Scheme