Methyl Acrylate → 4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid

Participants

Reaction Steps

A mixture of 4-bromo-1-naphthalenecarboxylic acid (which may be prepared by the methods described in Can. J. Chem. 1981, 59, 2629-41) (100 mg, 0.4 mmol), triethylamine (0.42 ml, 3 mmol), palladium acetate (12 mg, 0.04 mmol), triphenylphosphine (13 mg, 0.04 mmol) and methyl acrylate (1.19 ml, 0.11 mmol) in anhydrous DMF (8 ml) was heated to 100° C. for 4 h under nitrogen. The mixture was allowed to cool to room temperature, evaporated to dryness under reduced pressure and purified by aminopropyl cartridge, eluting with MeOH, followed by 4M HCl in dioxane and then 2M ammonia in MeOH. The ammonia in methanol fractions were combined to afford a residue that was partitioned between DCM and water, the DCM layers combined, dried over magnesium sulfate filtered and evaporated to afford the title compound (99 mg, 97%). LCMS RT=3.25 min, ES−ve m/z 255 (M−H)−.

Provenance & Evidence