Dimethylformamide → HCID 624632, compound

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Reaction Steps

To a solution of 2-[(3-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.452 g, potassium carbonate 0.583 g and dimethylformamide 5 ml, methyl p-toluene sulfonate 0.314 g was added. After the mixture was stirred for two hours at a temperature of 60° C., water 100 ml was added, and the mixture was extracted with ethyl acetate 50 ml twice. The ethyl acetate solution was washed with a saturated sodium chloride solution 50 ml twice, dehydrated with anhydrous magnesium sulfate, filtered and concentrated at a temperature of 40° C. under reduced pressure to obtain crude powder. The residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1) and the fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure to obtain crystals. The crystals were dissolved in ethyl acetate 2 ml and hexane 10 ml, and the solution was allowed to stand at room temperature for two hours. The precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 377.2 mg.

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