4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=0°C; 22 h;

1.1: O3 / CH2Cl2 / -78 °C 1.2: 90 percent / NaBH4 / methanol / 0 °C 2.1: DMAP / CH2Cl2 / 0 °C View Scheme

1: With 2,4,6-trimethyl-pyridine in dimethyl sulfoxide T=150°C; Oxidation; 0.666667 h; 2: With 1,8-diazabicyclo[5.4.0]undec-7-ene T=20°C; unknown; 48 h; 3: With sodium tetrahydroborate in methanol T=-20 - 20°C; Reduction;

2,6-dimethylpyridine in dichloromethane T=-40°C; Inert atmosphere;

1H-imidazole in dichloromethane; N,N-dimethyl-formamide a.) r.t., 24 h, b.) 55 deg C, 30 h;

1.1: 97 percent / pyridinium p-toluenesulfonate; pyridinium dichromate / CH2Cl2 / 6 h / 20 °C 2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C 3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C 3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C 4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C View Scheme

sodium iodide in acetone T=60 - 70°C; 6 h;