Benzyl Chloride → 2-(Benzyloxy)-6-chloropyridine

HRID 1471240

Reaktionsgleichung

Reaktionsgleichung von HRID 1471240
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([O:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1785160256-chloropyridin-2-ol

Produkt 1

HCID 112644642-(Benzyloxy)-6-chloropyridineAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a flask were added 5.0 g 6-chloro-2-hydroxypyridine, 5.3 g potassium carbonate and 75 ml N,N-dimethylformamide. After cooling to 5 C under nitrogen, 5.9 g of benzyl chloride were added drop wise and the reaction mixture was warmed to 60 C for 3 hours. After cooling to 10 C, the reaction mixture was quenched with 75 ml of water and the product was extracted with ethyl acetate and washed with water. Following solvent removal, the product was purified by silica gel chromatography using 5% ethyl acetate in hexane to give a clear colorless oil 7.9 g.

Aufarbeitung

  1. temperatureAfter cooling to 5 C under nitrogen
  2. temperaturethe reaction mixture was warmed to 60 C for 3 hours
  3. temperatureAfter cooling to 10 C
  4. customthe reaction mixture was quenched with 75 ml of water
  5. extractionthe product was extracted with ethyl acetate
  6. washwashed with water
  7. customFollowing solvent removal
  8. customthe product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f03e2f09d3db47349b11affb9d07dde9
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09011734B2

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