1: 23.7 percent / pyridine / Ambient temperature 2: 87 percent / immidazole / dimethylformamide / 16 h / Ambient temperature 3: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C 4: 17 g / pyridine / 8 h / 0 °C 5: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 6: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 7: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 8: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 9: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 10: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 11: 97 percent / PPTS / CH2Cl2 / Ambient temperature 12: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 13: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 14: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 15: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 16: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme

2,6-dimethylpyridine; sodium perchlorate in acetonitrile Electrolysis;