Selenium Dioxide → 1H-Indene-1,3(2H)-dione, 2,2-dihydroxy-4-nitro-

HRID 527125

Reaktionsgleichung

Reaktionsgleichung von HRID 527125
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1CC[C:8]2=[O:13])([O-:3])=[O:2].[Se](=O)=[O:15].[O:17]1[CH2:22][CH2:21][O:20]CC1>C(O)(=O)C>[OH:15][C:21]1([OH:20])[C:22](=[O:17])[C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[C:8]1=[O:13]

Komponenten

5

Edukt 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 905634-Nitroindan-1-one

Produkt 1

HCID 1577121H-Indene-1,3(2H)-dione, 2,2-dihydroxy-4-nitro-Ausbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 4-nitro-2,3-dihydro-1H-inden-1-one (4.00 g, 20.9 mmol) in 1,4-dioxane (40 ml) and glacial acetic acid (4 ml) was added with selenium dioxide (5.10 g, 46.03 mmol), and refluxed for 3 hrs. After filtration at high temperature, the filtrate was concentrated to afford 2,2-dihydroxy-4-nitro-2H-inden-1,3-dione (4.67 g, 100%). To a solution of 2,2-dihydoxy-4-nitro-2H-inden-1,3-dione (4.67 g, 20.9 mmol) in TFA (10 ml) was added isopropyl anisole (3.14 g, 20.9 mmol), followed by stirring at 60° C. for 6 hrs. The reaction mixture was concentrated in a vacuum, and extracted with aq. sodium bicarbonate and ethylacetate. The concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (1.19 mg, 16%).

Aufarbeitung

  1. temperaturerefluxed for 3 hrs
  2. filtrationAfter filtration at high temperature
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6ba55106408045e19731d2620be4363d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346749B2

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