hydrogen; silica gel; 5-palladium/activated carbon in ethyl acetate T=20°C; P=2942.29 Torr; 4 h; Autoclave;

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.25 h / -78 °C 1.2: 0.5 h / -78 °C 2.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 °C / |Inert atmosphere 3.1: N,N-dimethylamino-1,1,2,2-tetrafluoroethane; pyridine hydrogenfluoride / dichloromethane / 7 h / 20 - 80 °C / |Inert atmosphere 4.1: triphenylphosphine; potassium carbonate; palladium dichloride / tetrahydrofuran; water / 12 h / 85 °C 5.1: sodium hydroxide / water; methanol / 1.5 h / 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine; pyridine / toluene / 12.5 h / |Reflux 7.1: potassium carbonate / methanol / 0.5 h / 20 °C View Scheme