Acetic Anhydride → 2-acetoxymethyl-3-methyl-4-methoxy-pyridine

HRID 1623573Notes

Reaction equation

HRID 1623573 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N+:6]([O-])=[C:5]([CH3:10])[C:4]=1[CH3:11].[C:12]([O:15]C(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:15][CH2:10][C:5]1[C:4]([CH3:11])=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 10630707Pyridine, 4-methoxy-2,3-dimethyl-, 1-oxide

Product 1

HCID 105840092-acetoxymethyl-3-methyl-4-methoxy-pyridineYield 33.3%

Procedure

To 37.2 g of 4-methoxy-2,3-dimethylpyridine-1-oxide, 55.0 g (5.0 eq.) of acetic anhydride was added, and the mixture was allowed to react for 3 hours at 90 to 100° C. Acetic anhydride was distilled off, and then the resulting concentrated residue was purified on a silica gel column, to obtain 15.8 g of 2-acetoxymethyl-3-methyl-4-methoxy-pyridine as an oily matter.

Workup

  1. customto react for 3 hours at 90 to 100° C
  2. distillationAcetic anhydride was distilled off
  3. customthe resulting concentrated residue was purified on a silica gel column

Sources & evidence

ORD record
ord-5c451ea1cc1447b998985f3dbf44e61b
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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