Dimethylformamide → 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)-5-hexynyloxy]benzenepropanoic acid methyl ester

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A mixture of 1.14 g (3.37 mmol) of 2,3-dihydro-8-propyl-7-[[(trifluoromethyl)sulfonyl]oxy]-4H-1-benzopyran-4-one, 0.94 g (3.62 mmol) of 2-[(5-hexynyl)oxy]benzenepropanoic acid methyl ester, 4.9 mL of dry triethylamine, 0.197 g (0.28 mmol) of dichlorobis(triphenylphosphine)palladium (II), and 21 mL of dry dimethylformamide was stirred and heated at 100° C. for 3 hr. The mixture was cooled, poured into ice-water, and worked-up with ether in the usual manner. The orange-red, oily residue was flash chromatographed on silica gel. Elution with 1:1 hexane-ether gave 1.25 g (83%) of 2-[6-(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)-5-hexynyloxy]benzenepropanoic acid methyl ester as a yellow oil.

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