water in tetrahydrofuran; water; acetic acid T=80 - 90°C; 2 h;

1: 1.) EtMgBr, 2.) CuCl / 1.) THF, 40 deg C, 2.) THF, from 50 deg C to 55 deg C, 2 h 2: 52 percent / Bu4NF / tetrahydrofuran / 12 h 3: pyridine 4: NaI, Me3SiCl / acetonitrile 5: 1.) LiN(i-Pr)2, 2.) HMPA 6: H2, quinoline / Pd/BaSO4 / ethyl acetate 7: lithium t-butyl thiolate / dimethylformamide View Scheme

1: 75 percent / water / acetic acid; tetrahydrofuran; H2O / 2 h / 80 - 90 °C 2: 57 percent / Jones reagent / acetone / 0.5 h / Ambient temperature View Scheme