Acetic Anhydride → HCID 12397253, compound

HRID 1606306Notes

Reaction equation

HRID 1606306 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:17]=[CH:18]C(C)=[N+:20]([O-])[CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:5]([O:4][CH2:1][C:2]1[CH:18]=[CH:17][C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:21][N:20]=1)(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 123972525-Benzyloxy-2-methylpyridine 1-oxide

Product 1

HCID 12397253HCID 12397253, compound

Procedure

To 80 ml. of acetic anhydride stirred at 135°C. is added slowly 39.8 g. (0.185 mol) of the above N-oxide. The solution is stirred at this temperature for 30 minutes and then poured into 500 ml. of ice-water. After stirring the mixture for two hours it is extracted with a mixture of ethyl acetate and ether. The extract is washed with water, dried and evaporated to dryness. The residue is passed through an alumina column with ether as the eluent. Evaporation of the first fraction yields 2-acetoxymethyl-5-benzyloxypyridine as an oil.

Workup

  1. additionis added slowly 39.8 g
  2. additionpoured into 500 ml
  3. stirringAfter stirring the mixture for two hours it
  4. extractionis extracted with a mixture of ethyl acetate and ether
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated to dryness
  8. customEvaporation of the first fraction

Sources & evidence

ORD record
ord-5c3bb9eea54a4dc89d3962579a2d3d62
Source dataset
uspto-grants-1976_04
Patent number
US03952101

Reaction notes

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