water; iodine in acetonitrile 4 h; Heating;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 89 percent / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: 90 percent / H2; acetic acid / Pd(OH)2/C / methanol; H2O / 24 h / 20 °C / 760.05 Torr 3.1: 99 percent / trifluoroacetic acid / CH2Cl2 / 15 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 91 percent / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: 93 percent / H2; acetic acid / Pd(OH)2/C / methanol; H2O / 24 h / 20 °C / 760.05 Torr 3.1: 99 percent / trifluoroacetic acid / CH2Cl2 / 15 h / 20 °C View Scheme