1: 1.) n-BuLi / tetrahydrofuran / 0.17 h / -10 °C 2: 1.) n-BuLi; 2.) iodine / tetrahydrofuran / 4 h / -23 °C 3: 65 percent / BF3*OEt2 / CH2Cl2 4: 63 percent / n-BuLi / tetrahydrofuran / 0.02 h / -100 °C 5: 75 percent / 10percent HCl / methanol; H2O / 36 h / Heating 6: 95 percent / H2 / Pd/C 7: 84 percent / DEAD, PPh3 / tetrahydrofuran / Ambient temperature 8: 55 percent / tributyltin hydride, AIBN / toluene / Heating View Scheme

1: 1.) n-BuLi / tetrahydrofuran / 0.17 h / -10 °C 2: 1.) n-BuLi; 2.) iodine / tetrahydrofuran / 4 h / -23 °C 3: 65 percent / BF3*OEt2 / CH2Cl2 4: 63 percent / n-BuLi / tetrahydrofuran / 0.02 h / -100 °C 5: 75 percent / 10percent HCl / methanol; H2O / 36 h / Heating 6: 95 percent / H2 / Pd/C View Scheme