Acetic Anhydride → 2-Acetoxymethyl-6-benzyloxypyridine

HRID 1068471Notes

Reaction equation

HRID 1068471 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N+:10]=1[O-])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18]>>[C:17]([O:20][CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:10]=1)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 197444346-Benzyloxy-2-picoline 1-oxide

Product 1

HCID 211934372-Acetoxymethyl-6-benzyloxypyridine

Procedure

A mixture of 2-benzyloxy-6-methylpyridine N-oxide (3.4 g, 15.9 mmol) and acetic anhydride (125 mL) was heated under reflux for 1 h. The resulting solution was concentrated under vacuum, and the residue was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 10-20% ethyl acetate in hexane gradient. Collection and concentration of appropriate fractions provided 2-acetoxymethyl-6-benzyloxypyridine as colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe resulting solution was concentrated under vacuum
  4. customthe residue was partitioned between aqueous sodium bicarbonate and dichloromethane
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-131434c42ae64d43a81c974a65a891b0
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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