Acetic Anhydride → (4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl acetate

HRID 727899Notes

Reaction equation

HRID 727899 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N+:10]([O-])=[C:9]([CH3:14])[C:8]=1[CH3:15].[C:16]([O:19]C(=O)C)(=[O:18])[CH3:17]>>[C:16]([O:19][CH2:14][C:9]1[C:8]([CH3:15])=[C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:12]=[CH:11][N:10]=1)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 100133794-(3-Methoxypropoxy)-2,3-dimethyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 19600546(4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl acetate

Procedure

20 ml of acetic anhydride was added to 760 mg (3.6 mmol) of 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide to carry out the reaction at 90° C. for one hour. The reaction mixture was distilled to remove the acetic anhydride, followed by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was extracted with chloroform. The extract was concentrated to obtain 700 mg of 2-acetoxymethyl-4-(3-methoxypropoxy)-3-methylpyridine as a brown oil.

Workup

  1. customthe reaction at 90° C. for one hour
  2. distillationThe reaction mixture was distilled
  3. customto remove the acetic anhydride
  4. additionfollowed by the addition of a saturated aqueous solution of sodium hydrogencarbonate
  5. extractionThe obtained mixture was extracted with chloroform
  6. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-9c5b0d1ffbbd493daaf378fa7540fc51
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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