Bromoacetone → 7-Methoxy-2-methylindolizine

HRID 273327

Reaktionsgleichung

Reaktionsgleichung von HRID 273327
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1.Br[CH2:11][C:12](=O)[CH3:13].N12CCCN=C1CCCCC2>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:5]([CH:4]=1)=[CH:9][C:12]([CH3:13])=[CH:11]2

Komponenten

5

Edukt 3

HCID 11715BromoacetoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 47377584-Methoxy-2-methylpyridine

Produkt 1

HCID 529516187-Methoxy-2-methylindolizineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

4-Methoxy-2-methylpyridine (0.123 g, 1 mmol) and bromoacetone (0.16 mL, 1 mmol) were heated at 95° C. under N2 for 2 h. 1,8-Diazabicyclo-[5.4.0]-undec-7-ene (0.34 mL, 2.2 mmol) in benzene (10 mL) was added. The mixture was then refluxed under N2 for 1 h, poured into ice water, and then extracted with EtOAc. The combined organic layers were washed with water and dried. After the solvent was removed in vacuo, the residue was purified on a silica gel column eluting with EtOAc:Hexane (1:9) and EtOAc to give 7-methoxy-2-methylindolizine (0.050 g, 31%).

Aufarbeitung

  1. temperatureThe mixture was then refluxed under N2 for 1 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. customdried
  5. customAfter the solvent was removed in vacuo
  6. customthe residue was purified on a silica gel column
  7. washeluting with EtOAc:Hexane (1:9) and EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-6df95fb68b7c47248a73d1d03ad07ace
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456289B2

Verknüpfte Notizen

Wird geladen…