1: With chloro-trimethyl-silane; sodium iodide in acetonitrile 48 h; Reflux; 2: With water in acetonitrile T=20°C;

1: KOH, H2O / ethanol / 1 h / Heating 2: 88 percent / diethyl ether / 0.33 h View Scheme

1: lithium aluminium tetrahydride / diethyl ether / 3 h / 25 °C 2: pyridinium chlorochromate / dichloromethane / 4 h / 25 °C 3: triphenylphosphine / dichloromethane / 3 h / 25 °C 4: n-butyllithium / tetrahydrofuran / 2 h / -78 °C 5: silver hexafluoroantimonate / water / 70 °C View Scheme

1: 71 percent / lithium aluminium hydride / tetrahydrofuran / 2.5 h / Heating 2: 83 percent / o-iodoxybenzoic acid / ethyl acetate / 2 h / 80 °C View Scheme