I[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.CCN(CCOC1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl.C(#N)C.[C:39]([O:43][CH3:44])(=[O:42])[CH:40]=[CH2:41]>[Zn].O>[CH3:13][O:12][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][C:8]=1[O:10][CH3:11])[CH2:41][C:40]([C:39]([O:43][CH3:44])=[O:42])=[CH:4]2
2-Iodo-4,5-dimethoxybenzaldehyde (292 mg, 1.0 mmol), CoCl2 (dppe) complex (26.4 mg, 0.05 mmol), dppe (19.9 mg, 0.05 mmol) and zinc power (179.8 mg, 2.75 mmol) were placed in a vial, which was sealed with a septum and flushed several times with nitrogen. Acetonitrile (3 mL) and methyl acrylate (172 mg, 2.0 mmol) were then sequentially added and the mixture was heated at 80° C. overnight. Water was then added and the mixture was extracted with ethyl acetate. The organic extracts were concentrated under reduced pressure and the residue was purified by flash chromatography using petroleum ether/ethyl acetate 8:1 (v:v) as eluent to give methyl 5,6-dimethoxy-1H-indene-2-carboxylate (50 mg, 21%). LC-MS (ES-API); rt 7.89 min; m/z calculated for C13H14O4 [M+H]+ 235.1, found 235.1.
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