I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C.Cl>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:16]([O:15][C:11](=[O:14])/[CH:12]=[CH:13]/[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:17]
Under an argon atmosphere, to a solution of 3-iodobenzoic acid (20.2 g) in DMF (130 mL) were added ethyl acrylate (9.00 g), triethylamine (24 mL) and palladium (II) acetate (92 mg), and the mixture was stirred at 140° C. for 3 hr. The reaction mixture was cooled to room temperature, and 1N hydrochloric acid was added. The reaction mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (18.7 g) as an orange amorphous solid.
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