Selenium Dioxide → (R)-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde

HRID 338956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338956
[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2)[CH3:5].[Se](=O)=[O:19]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH:17]=[O:19])[CH:13]=[CH:12]2)[CH3:5]

Komponenten

5

Edukt 2

HCID 24007Selenium DioxideHCID 70982963(R)-8-(1-methoxypropan-2-yloxy)-2-methylquinoline

Produkt 1

HCID 86707475(R)-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehydeAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-8-(1-methoxypropan-2-yloxy)-2-methylquinoline (0.45 g, 1.9 mmol) in dioxane (35 mL) and water (0.35 mL) was added selenium dioxide (0.26 g, 2.3 mmol) and the resultant mixture heated at reflux for 2 hours. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and purified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes) to afford the title compound (0.42 g, 88%).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a plug of Celite®
  4. customto remove solids
  5. washrinsing with dichloromethane
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b6efd659ac0741f48cedd8092ed6c543
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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