1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / tetrahydrofuran / 35 - 65 °C / |Inert atmosphere; |Molecular sieve 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.17 h / 27 °C / |Inert atmosphere 2.2: 35 - 40 °C / |Inert atmosphere View Scheme

1.1: 1H-imidazole / dichloromethane / 15 h 1.2: 0 °C / pH 3 - 4 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C 2.2: 15 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C 4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 5.2: 24 h 6.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 6.2: 1 h / 20 °C 7.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 7.2: 3 h 8.1: Dess-Martin periodane / dichloromethane / 2 h 9.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1H-imidazole in N,N-dimethyl-formamide T=0°C; 1 h;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane 1.) -20 deg C, 1.5 h, 2.) room temperature, 16 h;

1H-imidazole in N,N-dimethyl-formamide T=-40°C; 2 h;