Ethyl 4-phenylbicyclo[2.2.2]oct-2-ene-1-carboxylate → Ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate

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Reaction Steps

Ethyl 4-phenylbicyclo[2.2.2]oct-2-ene-1-carboxylate (Intermediate 3; 26.3 g, 102.5 mmol) in absolute ethanol (600 mL) and 10% Pt on carbon (2.4 mg) were stirred under a balloon of hydrogen at ambient temperature overnight. The reaction mixture was filtered and the solvent removed under reduced pressure to leave a colourless oil which rapidly formed a white solid (22.179 g, 85.96 mmol, 84%) 1H NMR (CDCl3) δ 1.25 (3H, t), 1.83-1.96 (12H, m), 4.12 (2H, q), 7.15-7.20 (1H, m), 7.28-7.31 (4H, m); GC-MS EI m/e M+ 258.

Provenance & Evidence