Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][C:14]([CH3:16])=[CH2:15].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C.C(OCC)(=O)C.CCCCCC>C1C=CC=CC=1>[CH3:15][C:14]1([CH3:16])[C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[O:12][CH2:13]1A mixture of methyl 4-bromo-3-(2-methylallyloxy)benzoate (0.500 g, 1.754 mmol), tributyltin hydride (0.708 mL, 2.63 mmol), and AIBN (0.035 g, 0.210 mmol) in benzene (20 mL) was heated in a pressure tube at 120° C. for 22 h. The volatiles were removed under vacuum. The residue was diluted with ethyl acetate (100 mL) and shaken with 10% KF solution. The resulting precipitate was removed by suction filtration through CELITE®. The organic layer of the filtrate was separated, washed with saturated NaHCO3 solution and brine, and dried over anhydrous MgSO4. The desired product, methyl 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylate (0.131 g, 0.635 mmol, 36.2% yield) was isolated as a colorless oil with ISCO (40 g silica gel, 1-10% ethyl acetate/hexane).
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