Methanol → Methyl 6-cyanonaphthalene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester from Example 95 (1.50 g, 4.98 mmol) in 20 mL of anhydrous DMF was added palladium(II) acetate (33.53 mg, 0.15 mmol), triphenylphosphine (78.36 mg, 0.30 mmol), triethylamine (1.39 mL, 9.96 mmol) and 5 mL of methanol. This mixture was purged with carbon monoxide for ten minutes. The reaction mixture was then placed under balloon pressure of carbon monoxide and heated to 60° C. for 16 hours. The mixture was then diluted with brine, extracted with EtOAc (3×100 mL), extracts washed with 1N HCl (2×100 mL), dried over MgSO4, and concentrated under reduced pressure. Flash chromatography (hexane to 20% EtOAc/hexane) afforded the desired product as a white solid (525 mg, 50%).

Provenance & Evidence