1: With sodium hydroxide in ethanol T=77 - 80°C; 16 h; 2: With hydrogenchloride in ethanol; dichloromethane T=10 - 25°C;

hydrogenchloride; NaOH; citric acid in ethanol; n-heptane

hydrogenchloride; NaOH in ethanol

1.1: sodium salt of phosphorous acid; tri-tert-butyl phosphine / bis(dibenzylideneacetone)-palladium(0) / toluene; hexanes / 0.83 h / 23 °C / Inert atmosphere 1.2: 70 °C 2.1: hydrogenchloride / water; dimethyl sulfoxide / 40 - 75 °C 3.1: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 4.1: sodium hydroxide; water / ethanol / 80 °C View Scheme

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 3.1: dimethyl sulfoxide / 1 h / 30 - 40 °C 4.1: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 5.1: sodium hydroxide; water / ethanol / 80 °C View Scheme

1: thionyl chloride / 4-(N,N-dimethlyamino)pyridine / tert-butyl methyl ether / 1.5 h / 15 - 30 °C 2: dimethyl sulfoxide / 1 h / 30 - 40 °C 3: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 4: sodium hydroxide; water / ethanol / 80 °C 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 View Scheme

1: hydrogenchloride / water; dimethyl sulfoxide / 40 - 75 °C 2: tetra-n-octylammonium bromide; potassium hydroxide / water / 1 h / 70 °C 3: sodium hydroxide; water / ethanol / 80 °C View Scheme

1: thionyl chloride / toluene / 0.5 h / 60 °C 2: triethylamine; 4-(N,N-dimethlyamino)pyridine / toluene / 2 h 3: hydrogenchloride; water / acetonitrile / 40 - 45 °C View Scheme

thionyl chloride; triethylamine in dichloromethane; water; toluene