Hydrochloric Acid → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-oxo-1-propen-1-yl]benzoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-iodobenzoate (may be prepared as described in Description 112; 740 mg, 1.92 mmol) in N,N-dimethylformamide (5 ml) was added 3,3-bis(ethyloxy)-1-propene (0.88 ml, 5.8 mmol), potassium carbonate (397 mg, 2.87 mmol) and PdOAc2 (25.8 mg, 0.115 mmol). The reaction was heated in the microwave at 120° C. for 40 minutes, cooled and then 2M HCl (5 ml) was added and the mixture stirred for 20 minutes. The mixture was extracted with diethyl ether (2×10 ml), the organic layer dried (MgSO4), and the solvent removed in vacuo. Purification by column (Si, (solute, 6:1 cyclohexane/ethyl acetate) yielded the title compound. 163 mg.

Provenance & Evidence