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

HRID 2113378Notes

Reaction equation

HRID 2113378 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 112644642-(Benzyloxy)-6-chloropyridineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5aefd344b383459f9e051c4be9c9a6f2
Source dataset
uspto-grants-2009_04
Patent number
US07525717B2

Reaction notes

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