iodine; iodic acid in methanol; water 48 h; Heating;

1: hydrogenchloride / water; dichloromethane / 3 h / 0 - 40 °C 2: dimethyl sulfoxide / 1.5 h / 20 °C 3: potassium carbonate / ethanol; water / 1.5 h / 50 °C 4: potassium iodide; triethylamine / acetonitrile / 24 h / 20 - 60 °C 5: sodium hydroxide / ethanol; water / 6 h / |Reflux 6: thionyl chloride; triethylamine / dichloromethane / 1 h / 5 - 30 °C View Scheme

potassium carbonate in methanol; water 2 h; Heating;

1: 82 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature 2: Et3N / tetrahydrofuran / 48 h / 80 °C View Scheme

1: 82 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature 2: Et3N / tetrahydrofuran / 48 h / 80 °C View Scheme

1.1: 93 percent / I2; HIO3 / methanol; H2O / 48 h / 85 °C 2.1: 84 percent / CuI; PPh3; iPr2NH / Pd(PPh3)2Cl2 / 16 h / 25 °C 3.1: 90 percent / KOH / methanol; H2O / 20 h / 25 °C 4.1: 98 percent / Cp2TiMe2 / toluene / 16 h / 110 °C 5.1: HCOOH; NEt3 / Noyori's catalist / dimethylformamide / 7 h / 25 °C 5.2: methanol; H2O / 3 h / 25 °C 5.3: NaBH4 / methanol; H2O / 16 h / 25 °C View Scheme

1.1: iodine / dichloromethane / 15 h / 20 °C 2.1: potassium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 - 5 °C / Inert atmosphere 2.2: 17 h / 20 °C / Inert atmosphere; Reflux 3.1: potassium carbonate / methanol; water / 2 h / 20 °C 4.1: copper diacetate; palladium diacetate; potassium carbonate / toluene / 24 h / Inert atmosphere; Reflux View Scheme

1.1: iodine / dichloromethane / 15 h / 20 °C 2.1: potassium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 - 5 °C / Inert atmosphere 2.2: 17 h / 20 °C / Inert atmosphere; Reflux 3.1: potassium carbonate / methanol; water / 2 h / 20 °C 4.1: copper diacetate; palladium diacetate; potassium carbonate / toluene / 24 h / Inert atmosphere; Reflux View Scheme

2: 4 h / 130 °C View Scheme

1: 82 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature 2: tetrahydrofuran / 48 h / 80 °C View Scheme