1.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 1.2: 6 h / -78 - 20 °C / Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / methanol / 1 h / 20 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere 3.2: 4 h / 20 °C / Saturated solution 4.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere 5.1: hydrogenchloride / methanol / 4 h / 20 °C 6.1: palladium 10 on activated carbon; formic acid / methanol / 12 h / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -70 °C 1.2: -70 - 20 °C 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C View Scheme

sodium hydride; dimethyl sulfoxide 1.) room temp., 10 min; 2.) room ttemp., 2 h; Yield given. Multistep reaction. Yields of byproduct given;

sodium hexamethyldisilazane 1.) THF, reflux, 2 h, 2.) THF, a) -78 deg C, 2 h, b) RT, 12 h; Yield given. Multistep reaction;

n-butyllithium; triphenylphosphine in hexane

T=100°C; 12 h;

1: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 2: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

sodium amide in tetrahydrofuran 2 h; Heating;