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Reaction of 3-[1-(trimethylsilyloxy)vin-1-yl]furan with DMAD in toluene for 72 h afforded 4-hydroxybenzofuran-6,7-dicarboxylic acid dimethyl ester and 4-hydroxyphthalic acid dimethyl ester in 17% and 13% yield, respectively. The benzofuran comes from the reaction of DMAD with the furan 2,3-double bond 3-vinyl group diene system and the phthalate from the reaction of DMAD with the furan ring diene system. The ratio for the preference of these two systems in this case is 1.3, and for 5, as described above, is 2.4. The change of the silyl group had a small influence in the ratio. Unpublished results from F. R. Herrera and F. X. Talamás.
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