hydrogen; palladium on activated charcoal in ethyl acetate P=2068.6 Torr; 4 h;

1: NaH / benzene / 16 h / Ambient temperature 2: H2 / 10percent Pd/C / ethyl acetate / 4 h / 2068.6 Torr View Scheme

1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate in tetrahydrofuran T=-78°C; 0.25 h; Inert atmosphere; 2: With ethylene dibromide in tetrahydrofuran T=-78 - 20°C; Inert atmosphere; regioselective reaction;