1: With trimethylsilyl trifluoromethanesulfonate; diethylphosphinoethane in dichloromethane; toluene T=20°C; 1 h; Inert atmosphere; 2: With diisobutylaluminium hydride in hexane; dichloromethane; toluene T=0°C; 0.333333 h; Inert atmosphere; 3: With water; sodium hydrogencarbonate in methanol; hexane; dichloromethane; toluene T=40°C; 2 h; chemoselective reaction;

hydrogen; palladium 10 on activated carbon in o-xylene T=140°C; P=5688.78 - 5947.36 Torr; 7 - 8 h;

hydrogenchloride in water; acetone T=20°C; 15 h;

hydrogen; palladium on activated charcoal in ethanol T=20°C; 6 h;

1: 88 percent / toluene / 8 h / 110 °C 2: 50 percent / H2 / Pd/C / ethanol / 6 h / 20 °C View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 1.2: 19 h / 20 °C 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 24 h / 20 °C 3.1: hydrogenchloride / water; acetone / 15 h / 20 °C View Scheme

1: hydrogen / palladium 10 on activated carbon / ethanol / 24 h / 20 °C 2: hydrogenchloride / water; acetone / 15 h / 20 °C View Scheme

lithium hydroxide; water