hydrogen; palladium(II) oxide hydrate in methanol T=20°C; P=1034.32 Torr; 1 h; Inert atmosphere;

potassium hydroxide; water in methanol

1: 94 percent / PPTS / toluene 2: KOH; water / methanol View Scheme

1: 94 percent / PPTS / toluene 2: KOH; water / methanol View Scheme

1: 94 percent / PPTS / toluene 2: KOH; water / methanol View Scheme

1: hydrogenchloride / water; ethyl acetate / 10 h / 20 °C 2: triethylamine / dichloromethane / 20 °C / |Inert atmosphere 3: pyridinium p-toluenesulfonate / toluene / 4.33 h / 90 - 100 °C / |Inert atmosphere 4: hydrogen; palladium(II) oxide hydrate / methanol / 1 h / 20 °C / 1034.32 Torr / |Inert atmosphere View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -70 °C / |Inert atmosphere 1.2: 4.5 h / -70 °C / |Inert atmosphere 2.1: hydrogenchloride / water; ethyl acetate / 10 h / 20 °C 3.1: triethylamine / dichloromethane / 20 °C / |Inert atmosphere 4.1: pyridinium p-toluenesulfonate / toluene / 4.33 h / 90 - 100 °C / |Inert atmosphere 5.1: hydrogen; palladium(II) oxide hydrate / methanol / 1 h / 20 °C / 1034.32 Torr / |Inert atmosphere View Scheme

1: pyridinium p-toluenesulfonate / toluene / 4.33 h / 90 - 100 °C / |Inert atmosphere 2: hydrogen; palladium(II) oxide hydrate / methanol / 1 h / 20 °C / 1034.32 Torr / |Inert atmosphere View Scheme

Multistep reaction;

1: dicyclohexyl-carbodiimide; 4-(N,N-dimethlyamino)pyridine; toluene-4-sulfonic acid / dichloromethane / 20 °C / |Inert atmosphere 2: acetyl chloride / tetrahydrofuran; methanol / 2 h / 0 °C / |Inert atmosphere View Scheme