1: dimethyl sulfoxide / 1 h / 30 - 40 °C 2: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 3: sodium hydroxide; water / ethanol / 80 °C View Scheme

1.1: dimethyl sulfoxide / 1 h / 30 - 40 °C 1.2: 0.5 h 2.1: potassium hydroxide; tetra-n-octylammonium bromide / water / 1 h / 70 °C 3.1: sodium hydroxide; water / ethanol / 80 °C 4.1: thionyl chloride / toluene / 0.5 h / 60 °C 5.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / toluene / 2 h 6.1: hydrogenchloride; water / acetonitrile / 40 - 45 °C View Scheme

thionyl chloride; 4-(N,N-dimethlyamino)pyridine in tert-butyl methyl ether T=15 - 30°C;

thionyl chloride; aq. NaOH; 4-(N,N-dimethlyamino)pyridine in water

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 15 - 40 °C 1.2: 0.5 h / 40 - 50 °C 2.1: thionyl chloride / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 1.5 h / 15 - 30 °C View Scheme

1: triethylamine / tetrakis (triphenylphosphine) palladium (0) / methanol; acetonitrile 2: sodium hydroxide; lithium aluminum hydride / tetrahydrofuran; water 3: 4-(N,N-dimethlyamino)pyridine / water View Scheme

1: sodium hydroxide; lithium aluminum hydride / tetrahydrofuran; water 2: thionyl chloride; sodium hydrogencarbonate / dichloromethane View Scheme

1: sodium tetrahydroborate; methanol 2: thionyl chloride / dichloromethane / 3 h / 20 °C / Cooling with ice View Scheme

1: dimethyl sulfoxide / 1 h / 30 - 40 °C 2: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 3: sodium hydroxide; water / ethanol / 80 °C 4: thionyl chloride / toluene / 60 °C 5: triethylamine / dichloromethane / 0 - 20 °C 6: hydrogen / 5 palladium on charcoal / tetrahydrofuran / 96 h / 50 °C / 2250.23 - 3000.3 Torr / autoclave; Inert atmosphere View Scheme

1: dimethyl sulfoxide / 1 h / 30 - 40 °C 2: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C View Scheme