Quinoline → HCID 68479074, compound

Participants

Reaction Steps

Quinoline (27.5 μL, 0.232 mmol) and 10% Pd/BaSO4 (4.90 mg, 0.0461 mmol) were added to a stirred solution of (4E)-12-methyloxacyclotetradec-4-en-8-yn-2-one (256 mg, 1.16 mmol) in ethanol (20 mL). The reaction flask was flushed with argon followed by hydrogen, and the reaction mixture was stirred under hydrogen atmosphere at room temp. and ambient pressure. After 5 h, GC-monitoring indicated complete conversion, upon which the catalyst was filtered off through a pad of Celite and washed with ethanol. The solvent was removed under reduced pressure, and the resulting residue purified by chromatography on silica gel [30 g; pentane-Et2O (20:1); Rf=0.60 in pentane-Et2O (5:1)] to furnish (4E,8Z)-12-methyloxacyclotetradeca-4,8-dien-2-one (223 mg, 86%) as a colourless odoriferous liquid.

Provenance & Evidence