1.1: 85 percent / pyridine N-oxide; NaHCO3 / toluene / 4 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -20 °C 2.2: 61 percent / tetrahydrofuran; hexane / 2 h / Heating 3.1: 543 mg / Et2Zn / CH2Cl2 / 49 h / -20 - 25 °C 4.1: 310 mg / HCl / methanol / 16 h / 25 °C 5.1: 69 percent / pyridinium dichromate / dimethylformamide / 0 - 25 °C View Scheme

1.1: 85 percent / pyridine N-oxide; NaHCO3 / toluene / 4 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -20 °C 2.2: 61 percent / tetrahydrofuran; hexane / 2 h / Heating 3.1: 543 mg / Et2Zn / CH2Cl2 / 49 h / -20 - 25 °C 4.1: 310 mg / HCl / methanol / 16 h / 25 °C 5.1: 69 percent / pyridinium dichromate / dimethylformamide / 0 - 25 °C 6.1: diethyl ether View Scheme