1: aq. KOH / ethane-1,2-diol / 8 h / Heating 2: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C 3: 48percent aq. HBr, CH3CO2H / 2 h / Heating 4: NaBH4 / ethanol / 0.5 h 5: p-toluenesulfonic acid / benzene / 1 h / Heating 6: pyridine / 3 h 7: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 8: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 99.7 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 2: 98.6 percent / Et3N / CH2Cl2 / 0.25 h / 0 - 5 °C 3: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating 4: aq. KOH / ethane-1,2-diol / 8 h / Heating 5: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C 6: 48percent aq. HBr, CH3CO2H / 2 h / Heating 7: NaBH4 / ethanol / 0.5 h 8: p-toluenesulfonic acid / benzene / 1 h / Heating 9: pyridine / 3 h 10: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 11: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 48percent aq. HBr, CH3CO2H / 2 h / Heating 2: NaBH4 / ethanol / 0.5 h 3: p-toluenesulfonic acid / benzene / 1 h / Heating 4: pyridine / 3 h 5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 6: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C 2: 48percent aq. HBr, CH3CO2H / 2 h / Heating 3: NaBH4 / ethanol / 0.5 h 4: p-toluenesulfonic acid / benzene / 1 h / Heating 5: pyridine / 3 h 6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 7: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating 2: aq. KOH / ethane-1,2-diol / 8 h / Heating 3: 53 percent / polyphosphoric acid / 2 h / 100 - 105 °C 4: 48percent aq. HBr, CH3CO2H / 2 h / Heating 5: NaBH4 / ethanol / 0.5 h 6: p-toluenesulfonic acid / benzene / 1 h / Heating 7: pyridine / 3 h 8: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 9: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

in den Faeces von Kaninchen, Ratten und Maeusen nach intraperitonealer oder intravenoeser Injektion;

phenol sulfatase T=37°C; 5 h; pH 5.0, in 0.2M acetate buffer, in dark;

1.1: palladium diacetate; potassium carbonate; triphenylphosphine / ethylene glycol dimethyl ether; water / 20 °C / Inert atmosphere 1.2: 23 h / Inert atmosphere; Reflux 2.1: (1,2,3,4,5-pentaphenylferrocen-1'-yl)-di-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0) / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: sodium hydroxide / ethanol; water / 1 h / Reflux 4.1: methanesulfonic acid / 1 h / 50 °C 5.1: pyridine / dichloromethane / 0.17 h / 20 °C 5.2: -78 - 20 °C 6.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 7.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 8.1: platinum (II) chloride / toluene / 80 °C 9.1: boron tribromide View Scheme

1.1: pyridine / dichloromethane / 0.17 h / 20 °C 1.2: -78 - 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 3.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 4.1: platinum (II) chloride / toluene / 80 °C 5.1: boron tribromide View Scheme

1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 2: platinum (II) chloride / toluene / 80 °C 3: boron tribromide View Scheme