1: H2 / Pd/CaCO3/Pb / benzene / 12 h / 760 Torr 2: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 3: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

hydrogen; Lindlar's catalyst in benzene P=760 Torr; 12 h; Yield given;

<b>Multi-step reaction with 3 steps<br /> </b>1: H⁽¹⁺⁾ <br />2: CH₃Li / tetrahydrofuran; hexamethylphosphoric acid triamide<br />3: P(C₆H₅)3*Br₂ / CH₂Cl₂ <br /> <br /> &nbsp;