[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1I)[C:8]([O:10][CH3:11])=[O:9])[CH:2]=[CH2:3].C([O-])([O-])=O.[Na+].[Na+].C([O-])=O.[Na+]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:3][C:2]1[C:14]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=2[O:4][CH:1]=1Methyl 3-(allyloxy)-4-iodobenzoate (2.0 g, 6.28 mmol) is dissolved in DMF (15 ml), treated with Pd(OAc)2 (71 mg, 0.31 mmol), Na2CO3 (1.67 g, 15.7 mmol), sodium formate (427 mg, 6.28 mmol), and n-Bu4NCl.H2O (1.92 g, 6.92 mmol) and stirred at 80° C. for 2 days. The mixture is then filtered, the liquor is diluted with EtOAc (75 ml) and washed with 50% saturated NaCl (4×25 ml) followed by 5% HCl (25 ml). The organic layer is dried (Na2SO4), filtered, and concentrated to a brown oil. The crude material is chromatographed over 50 g slurry-packed silica gel, eluting with 20% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 797 mg (67%) of methyl 3-methyl-1-benzofuran-6-carboxylate as a pale oil. HRMS (FAB) calcd for C11H10O3+H: 191.0708, found 191.0714 (M+H)+.
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