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

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 1.2: 68 percent / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 99 percent / hydrogen / Pd/C / ethanol / 6 h / 20 °C View Scheme

1.1: 99 percent / triphenylphosphine / CH2Cl2 / 0.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.2: 68 percent / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 99 percent / hydrogen / Pd/C / ethanol / 6 h / 20 °C View Scheme

1: diethyl ether; NaNH2; liquid NH3 / anschliessendes Behandeln mit (+-)-2,2,6-Trimethyl-cyclohexanon 2: palladium/CaCO3; ethanol / Hydrogenation View Scheme