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

HRID 486817Notes

Reaction equation

HRID 486817 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]([CH3:11])=[CH:4][N+:3]=1[O-].CN(C1C=CC=CN=1)C.[C:22]([O:25]C(=O)C)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([O:25][CH2:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[C:5]([CH3:11])=[CH:4][N:3]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 30.06 g (0.18 mole) of 2,3,5-trimethyl-4-methoxypyridine N-oxide in 100 ml of methylene chloride was added slowly (over approximately one hour) over a solution of 0.38 g of dimethylaminopyridine in 53.4 ml (0.565 mole) of acetic anhydride, heated to 90°-95° C., with the temperature being held within the abovementioned range and the methylene chloride being removed by distillation. At the end of the addition, the distillation was continued for a further 10 minutes, the mixture was cooled to below 90° C. and 7.5 ml of water were added slowly, holding the temperature below 90° C. Crude 2-acetoxymethyl-3,5-dimethyl-4-methoxypyridine was obtained by distillation at reduced pressure and was used directly as starting product for the hydrolysis (Example 2).

Workup

  1. temperatureheated to 90°-95° C., with the temperature
  2. customthe methylene chloride being removed by distillation
  3. additionAt the end of the addition
  4. distillationthe distillation
  5. temperaturethe mixture was cooled to below 90° C.
  6. addition7.5 ml of water were added slowly
  7. customthe temperature below 90° C

Sources & evidence

ORD record
ord-10c8b20b82b2402689c0376615a24def
Source dataset
uspto-grants-1994_03
Patent number
US05292886

Reaction notes

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