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

HRID 703182Notes

Reaction equation

HRID 703182 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:10][C:11]1[C:16]([CH3:17])=[CH:15][N+:14]([O-])=C(C)[CH:12]=1)[CH3:9]>C(Cl)(Cl)Cl>[C:5]([O:4][CH2:1][C:2]1[CH:12]=[C:11]([O:10][CH2:8][CH3:9])[C:16]([CH3:17])=[CH:15][N:14]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 221514414-Ethoxy-2,5-dimethylpyridine 1-oxide

Product 1

HCID 22151443(4-Ethoxy-5-methyl-2-pyridyl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 ml of acetic anhydride were added dropwise at room temperature to solutio of 7.8 of 4-ethoxy-2.5-dimethylpyridine 1-oxide in 30 ml of chloroform. After boiling under reflux for 3 hours the solution was evaporated, the residue was dissolved in 50 ml of toluene and again evaporated. The residue was taken up in 50 ml of ethyl acetate, whereupon the solution was extracted three times with 20 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. The product was chromatographed on 50 g of silica gel with ether and there was obtained (4-ethoxy-5-methyl-2-pyridyl)methyl acetate in the form of an oil.

Workup

  1. temperatureunder reflux for 3 hours the solution
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in 50 ml of toluene
  4. customagain evaporated
  5. extractionwas extracted three times with 20 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 50 g of silica gel with ether

Sources & evidence

ORD record
ord-add17029bf6a45eb8d062008a35745a4
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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