Acetic Anhydride → (4-Methoxy-5-methyl-2-pyridyl)methyl acetate

HRID 703177Notes

Reaction equation

HRID 703177 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][N+:13]([O-])=C(C)[CH:11]=1>C(Cl)(Cl)Cl>[C:5]([O:4][CH2:1][C:2]1[CH:11]=[C:10]([O:9][CH3:8])[C:15]([CH3:16])=[CH:14][N:13]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 151634614-Methoxy-2,5-dimethylpyridine 1-oxide

Product 1

HCID 22151432(4-Methoxy-5-methyl-2-pyridyl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

55 ml of acetic anhydride were added dropwise at room temperature to a solution of 19.9 g of 4-methoxy-2,5-dimethylpyridine 1-oxide in 75 ml of chloroform. After boiling under reflux for 2 hours the solution was evaporated, the residue was dissolved in 100 ml of toluene and again evaporated. The residue was taken up in 100 ml of ethyl acetate and the solution was extracted three times with 50 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. The product was chromatographed on 100 g of silica gel with ether and there was obtained (4-methoxy-5-methyl-2-pyridyl)methyl acetate in the form of an oil.

Workup

  1. temperatureunder reflux for 2 hours the solution
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in 100 ml of toluene
  4. customagain evaporated
  5. extractionthe solution was extracted three times with 50 ml of saturated sodium bicarbonate solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe product was chromatographed on 100 g of silica gel with ether

Sources & evidence

ORD record
ord-435ca48d83024072a1f83af87e05e81a
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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