1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / 0 °C 3: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere 4: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 3 h / 0 - 20 °C / pH 7 / aq. phosphate buffer View Scheme

1H-imidazole; 4-(N,N-dimethlyamino)pyridine in N,N-dimethyl-formamide T=20°C; 3 h;