1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C 2: bis(1,1-diphenylphosphino)methane; tetracarbonylbis(μ-chloro)dirhodium(I) / ethylene glycol dimethyl ether / 16 h / 65 °C / |Inert atmosphere View Scheme

1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / |Reflux 2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.2: 1 h / 0 °C 3.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 4.1: acetic acid / methanol / 1 h / 0 - 20 °C 4.2: 3 h / 0 - 20 °C 5.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C 6.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / |Inert atmosphere View Scheme

1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / |Reflux 2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.2: 1 h / 0 °C 3.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 4.1: acetic acid / methanol / 1 h / 0 - 20 °C 4.2: 3 h / 0 - 20 °C 5.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C View Scheme

sodium hydrogencarbonate; Dess-Martin periodane in dichloromethane T=20°C; 0.333333 h;