hydrogen; palladium on activated charcoal in ethanol T=20°C; 20 h;

1: 81 percent / 1.5 M diisobutylaluminium hydride / toluene / 2.5 h / -78 °C 2: 81 percent / H2 / 10percent Pd/C / ethanol; ethyl acetate / 3 h / 2250.2 Torr / Ambient temperature View Scheme

Multi-step reaction with 2 steps 1.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.25 h / -70 °C1.2: 47 percent / toluene; tetrahydrofuran / 0.5 h / -70 °C2.1: potassium hexamethyldisilazane / toluene; tetrahydrofuran / 0.5 h / -70 °C2.2: 13 percent / oxodiperoxymolybdenum(pyridine)(HMPTA) / toluene; tetrahydrofuran / 2 h / -70 °C