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

HRID 657003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657003
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH: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+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH: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 688097807-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

Produkt 1

HCID 59397833(7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehydeAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 7-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone (4.14 g, 0.019 mol) in 1,4-dioxane (80 ml) and water (40 ml) under N2 was added sodium periodate (9.5 g; 0.044 mol) and osmium tetroxide (10 ml, 4% aqueous solution) and stirred overnight. The reaction was concentrated and partitioned in 20% MeOH/DCM (300 ml) and water (200 ml). The organic layer was dried over magnesium sulphate, filtered, and concentrated. The product was obtained after column chromatography (neat ethyl acetate) to yield g (71%) of the title compound as a green solid.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. custompartitioned in 20% MeOH/DCM (300 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was obtained after column chromatography (neat ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f361fc962ee64c8ab2923ca82377251c
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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