[C:1]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1.CCOCC>[C:1]([C:5]1[C:13]2[O:12][CH:11]=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]A solution of 0.31 g (1.22 mmol) of 7-Carbomethoxy dihydrobenzofuran and 1.66 g (3.3 mmol) of DDQ in 25 mL of toluene was heated at reflux for 7 h. The reaction mixture was then cooled to rt, diluted with ether, and washed with 3×30 mL of sat'd NaHCO3 solution. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 9:1) to give 0.25 g of the title compound.
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