Hydrochloric Acid → 2-(4'-Methoxyphenyl)-5-octyloxypyridine

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Reaction Steps

To a flask outfitted with a reflux condenser was added 6B (300 mg), 6A (600 mg), and palladium tetrakis(triphenylphosphine) (62 mg). To this mixture was added toluene (4 ml) and a sodium carbonate solution (2M, 4.5 ml). This solution was refluxed for 16 hrs, at which time it was acidified with hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate and potassium carbonate. The solvent was removed in vacuo. The product purified by flash chromatography using 20% ethyl acetate in hexanes as the eluent to give a yellow liquid.

Provenance & Evidence