Sodium periodate → (7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde

HRID 657157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657157
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=C)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:18].[Na+]>CC(O)CC.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=[O:18])=[CH:5][CH:4]=1

Komponenten

6

Edukt 2

HCID 23667635Sodium periodateHCID 68810513HCID 68810513, Verbindung

Produkt 1

HCID 59398142(7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehydeAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6568(+-)-2-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 7-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinoxalinone (1.03 g, 4.75 mmol) and sodium periodate (4.68 g, 21.8 mmol) in 2-butanol (20 mL) and water (40 mL) was treated with osmium tetroxide (4% solution in water, 1.1 mL) and the mixture was stirred for 3.75 h. The butanol was evaporated and the residue was diluted with water and extracted with dichloromethane, then with dichloromethane/THF. The extracts were dried and evaporated, and the residue was chromatographed on silica eluted with 50-100% ethyl acetate/hexane to give the aldehyde (0.68 g, 66%).

Aufarbeitung

  1. customThe butanol was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted with dichloromethane
  4. customThe extracts were dried
  5. customevaporated
  6. customthe residue was chromatographed on silica
  7. washeluted with 50-100% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4a9a8111e57e4cd38a30cf0f7585f13a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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