1: 91 percent / acetonitrile / 14 h, room temperature then 24 h, 50 degC 2: 1.) n-BuLi / 1.) THF/HMPA/hexane, -78 degC, 20 min; 2.) THF/HMPA/hexane/Et2O, -78 degC, 1 h then room temperature, 1 h 3: H2 / PtO2 / ethanol / 1.75 h / Ambient temperature View Scheme

sodium thiosulfate; sodium iodide in acetone Ambient temperature;

p-toluenesulfonyl chloride; sodium iodide 1.)pyridine, 2.)acetone; Multistep reaction;

sodium iodide in acetone Yield given;

1: nickel boride 2: N(C2H5)3 3: NaI / acetone View Scheme

1: toluene / anion exchange by AG 1-X8 resin 2: 46 percent / nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 3: K2CO3 / H2O; methanol View Scheme