1,4-Dioxane → 7-(Oxetan-3-yl)quinoline-2-carbaldehyde

HRID 339078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339078
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]3[CH2:15][O:14][CH2:13]3)=[CH:7][CH:8]=2)[N:3]=1.[O:16]1CCOCC1>O>[O:14]1[CH2:13][CH:12]([C:6]2[CH:5]=[C:4]3[C:9]([CH:10]=[CH:11][C:2]([CH:1]=[O:16])=[N:3]3)=[CH:8][CH:7]=2)[CH2:15]1

Komponenten

4

Edukt 2

HCID 312751,4-DioxaneHCID 867075512-Methyl-7-(oxetan-3-yl)quinoline

Produkt 1

HCID 867075527-(Oxetan-3-yl)quinoline-2-carbaldehydeAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-Methyl-7-(oxetan-3-yl)quinoline (0.020 g, 0.100 mmol) was dissolved in dioxane (5 mL) and water (0.05 mL). The reaction was treated with SeO2 (0.013 g, 0.120 mmol) and the mixture was heated to reflux for 2 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure to give 7-(oxetan-3-yl)quinoline-2-carbaldehyde (0.020 g, 0.0938 mmol, 93.4% yield) as a solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8a3a255a5aaa4105b2c3fb296f73aa21
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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