1: -78 °C 2: LiOH 3: NaI / acetone 5: 81 percent / KN(SiMe3)2 / tetrahydrofuran / 0 °C 6: 98 percent / pyridine, (HF)x / tetrahydrofuran 7: 68 percent / DEAD, PH3P / benzene 8: 68 percent / Ce(NH4)2(NO3)6 / H2O; acetonitrile 9: HOAc / tetrahydrofuran; H2O / 60 °C View Scheme

1: tetra-(n-butyl)ammonium iodide; sodium carbonate; sodium iodide / tetrahydrofuran / 48 h / Inert atmosphere; Reflux 2: sodium tetrahydroborate; acetic acid / acetonitrile / 3 h / 20 °C / Inert atmosphere View Scheme

T=-78°C;

copper(l) iodide 1.) THF, ether, -10 deg C, 2.) THF, ether, -78 deg C, 1 h; Yield given. Multistep reaction;