Ethyl Bromide → 3-Ethoxy-2-methylpyridine

HRID 1956412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956412
[Na].[OH:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH3:12]>C(O)C>[CH2:11]([O:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:12]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 707192-Methylpyridin-3-olHCID 5360545Sodium

Produkt 1

HCID 128750153-Ethoxy-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Sodium metal (46.2 g) was dissolved in absolute ethanol (1 l) with stirring under nitrogen. 3-Hydroxy-2-methylpyridine (200 g prepared as described in C.A. 48, P4597 h) was added. The mixture was stirred at ambient temperature for 30 minutes and then a solution of bromoethane (150 ml) in absolute ethanol (100 ml) was added. The mixture was boiled under reflux for 5 hours then cooled and filtered. The filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic layer was separated off and the aqueous layer extracted with dichloromethane. The combined organic extracts were dried and evaporated. The residue was distilled to give 3-ethoxy-2-methyl-pyridine b.p. 80°-84° C. (20 mmHg).

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 30 minutes
  2. temperatureunder reflux for 5 hours
  3. temperaturethen cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customthe residue partitioned between dichloromethane and water
  7. customThe organic layer was separated off
  8. extractionthe aqueous layer extracted with dichloromethane
  9. customThe combined organic extracts were dried
  10. customevaporated
  11. distillationThe residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-c05ac5b4791440ab8ecb0fd3523bb3b1
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780482

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