Acetic Anhydride → 2-(Acetoxymethyl)-4-methoxy-3,5-dimethylpyridine

HRID 979854Notes

Reaction equation

HRID 979854 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][O:9][C:10]1[C:15](C)=[CH:14][N+:13]([O-])=[C:12](C)[C:11]=1[CH3:19]>C(Cl)(Cl)Cl>[C:5]([O:4][CH2:1][C:2]1[C:15]([CH3:14])=[C:10]([O:9][CH3:8])[C:11]([CH3:19])=[CH:12][N:13]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxide

Product 1

HCID 50672892-(Acetoxymethyl)-4-methoxy-3,5-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

215 ml of acetic anhydride were added dropwise at room temperature to a solution of 81.5 g of 4-methoxy-2,3,5-trimethylpyridine 1-oxide in 290 ml of chloroform. After boiling under reflux for 4 hours the solution was evaporated, the residue was dissolved in 200 ml of toluene and again evaporated. The residue was taken up in 500 ml of ethyl acetate and extracted three times with 250 ml of saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. The product which remains behind as the residue was chromatographed on 400 g of silica gel with ether. There was obtained (4-methoxy-3,5-dimethyl-2-pyridyl)methyl acetate in the form of an oil.

Workup

  1. temperatureunder reflux for 4 hours the solution
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in 200 ml of toluene
  4. customagain evaporated
  5. extractionextracted three times with 250 ml of saturated sodium bicarbonate solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customevaporated in vacuo
  8. customwas chromatographed on 400 g of silica gel with ether

Sources & evidence

ORD record
ord-3a3f5df45cdc469da2f1e37011b5d7af
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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