Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid → Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid

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Reaction Steps

Compound 11A (600 mg, 3.99 mmol) was dissolved in EtOAc (5 mL), 5% Pd/C (12 mg) was added and the mixture was stirred under a hydrogen balloon for 1.5 h. The reaction mixture was filtered through a pad of celite and concentrated under reduced pressure to give 600 mg of compound 11B as a yellow oil. No further purification was necessary. HPLC conditions: 95% at 2.65 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm). C. Bicyclo[2.2.2]oct-2-ene-2-carbonyl chloride (11C)

Provenance & Evidence