[OH:1][C:2]1[C:3](=[O:15])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1I)=[C:8]([OH:14])[CH:7]=[CH:6][CH:5]=2.[CH3:16][CH:17]([OH:20])[C:18]#[CH:19]>N1C=CC=CC=1.[Cu]=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:20][CH:17]([C:18]1[O:1][C:2]2[C:3](=[O:15])[C:4]3[C:9]([C:10](=[O:13])[C:11]=2[CH:19]=1)=[C:8]([OH:14])[CH:7]=[CH:6][CH:5]=3)[CH3:16]To a solution of 2,5-dihydroxy-3-iodonaphthalene-1,4-dione (30 mg, 0.095 mmol) in pyridine (3.5 ml) were added copper oxide (1) (13.5 mg, 0.095 mmol), 3-butyn-2-ol (75 μl, 0.949 mmol) and dichlorobis(triphenylphosphine)palladium (2 mg, 3 mol %), and the mixture was stirred at 80° C. of the reaction temperature for 30 minutes. The reaction solution was cooled to room temperature, and then the reaction was quenched by the addition of 2M hydrochloric acid. The reaction solution was extracted with chloroform. The organic layer was washed with ice water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione (17.2 mg, 70%) as a yellow solid.
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