n-butyllithium in tetrahydrofuran; hexane 1.) -100 deg C, 1 h, 2.) -85 deg C, 1 h;

1: 85 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 3 h, 2.) -78 deg C to r.t., 12 h 2: 75 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -100 deg C, 1 h, 2.) -85 deg C, 1 h View Scheme

1: 61 percent / BF3*OEt2, EtOH / nitromethane / 2 h / 20 °C 2: 92 percent / diethyl ether / 3 h / Heating 3: 80 percent / p-toluenesulfonic acid / benzene / 12 h / Heating View Scheme

n-butyllithium 1.) Et2O, -70 deg C, 30 min, 2.) Et2O, a.) -70 deg C, 2 h, b.) 25 deg C, overnight; Yield given. Multistep reaction;

indium; methyllithium 1.) 1,4-dioxane, 2.) 0 deg C, 30 min; room temperature, 2 h, 3.) 1,4-dioxane, 0 deg C, 1 h, room temperature, 1 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;