1,4-Dioxane → 7-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde

HRID 339062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339062
[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH3:22])=[N:19]2)=[CH:14][C:13]=1[F:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:24]1CCOCC1>O>[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]=[O:24])=[N:19]2)=[CH:14][C:13]=1[F:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 312751,4-DioxaneHCID 709833797-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline

Produkt 1

HCID 867075467-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehydeAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline (2.74 g, 8.17 mmol) in dioxane (24 mL) and water (0.24 mL) was added SeO2 (0.997 g, 8.98 mmol). The reaction mixture was heated at reflux for 4 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure and The residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc) to give 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde (2.69 g, 94%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-ac39514543f8479997cab4ae1c92463c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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