3-Butyn-2-ol → 5-Hydroxy-2-(1-Hydroxyethyl)Naphtho(2,3-B)Furan-4,9-Dione

HRID 2369453Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

temperatureThe reaction solution was cooled to room temperature
customthe reaction was quenched by the addition of 2M hydrochloric acid
extractionThe reaction solution was extracted with chloroform
washThe organic layer was washed with ice water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-062613be72de45dc84438e1c77943c55
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703979B2

Reaction notes

Loading…