Lithium acetate → Methyl 2-(quinolin-5-yl)propanoate

Participants

Reaction Steps

A solution of tris(dibenzylideneacetone)-dipalladium (65 mg, 0.14 mmol), 1,1′-bis(diphenylphosphino)ferrocene(155 mg, 0.28 mmol) and lithium acetate(2.8 g, 27.6 mmol) in THF (50 mL) was stirred at room temperature for 5 minutes. To this mixture was added 5-quinolyl trifluoromethanesulfonate and [(E)-1-methoxy-1-propenyl]oxy(trimethyl)silane. The resulting mixture was heated at reflux for 24 hours and then allowed to cool to room temperature. The mixture was filtered, the residue was washed with THF(50 mL) and the solvent was removed under reduced pressure. Following a short silica column and aqueous workup, methyl 2-(5-quinolyl)propanoate was purified by HPLC yield 250 mg, 17%. HPLC (10% to 90% acetonitrile in 0.1N aqueous ammonium acetate over 10 min at 2 mL/min using a Waters Symmetry C18, 150×4.6 mm column) 6.89 min.

Provenance & Evidence