Acetic Anhydride → (4-Ethoxy-3,5-dimethyl-2-pyridyl)methyl acetate

HRID 703171Notes

Reaction equation

HRID 703171 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:10][C:11]1[C:16](C)=[CH:15][N+:14]([O-])=[C:13](C)[C:12]=1[CH3:20])[CH3:9]>C(Cl)(Cl)Cl>[C:5]([O:4][CH2:1][C:2]1[C:16]([CH3:15])=[C:11]([O:10][CH2:8][CH3:9])[C:12]([CH3:20])=[CH:13][N:14]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 221514664-Ethoxy-2,3,5-trimethylpyridine 1-oxide

Product 1

HCID 22151469(4-Ethoxy-3,5-dimethyl-2-pyridyl)methyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

75 ml of acetic anhydride were added dropwise at room temperature to a solution of 31,3 g of 4-ethoxy-2,3,5-trimethylpyridine 1-oxide in 100 ml of chloroform. After boiling under reflux for 16 hours the solution was evaporated, the residue was dissolved in 100 ml of toluene and again evaporated. The residue was taken up in 250 ml of ethyl acetate, whereupon it was extracted three times with 100 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. The product was chromatographed on 170 g of silica gel with ether. There was obtained (4-ethoxy-3,5-dimethyl-2-pyridyl)methyl acetate in the form of an oil.

Workup

  1. temperatureunder reflux for 16 hours the solution
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in 100 ml of toluene
  4. customagain evaporated
  5. extractionwas extracted three times with 100 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 170 g of silica gel with ether

Sources & evidence

ORD record
ord-0d59611c01824a99b83f95dfbde0e308
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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