Acetic Anhydride → 2-Acetoxymethyl-3-methyl-4-propoxy-pyridine

HRID 1623579Notes

Reaction equation

HRID 1623579 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][N+:8]([O-])=[C:7]([CH3:12])[C:6]=1[CH3:13])[CH2:2][CH3:3].[C:14]([O:17]C(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:17][CH2:12][C:7]1[C:6]([CH3:13])=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:10]=[CH:9][N:8]=1)(=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 150355372,3-Dimethyl-4-propoxypyridine 1-oxide

Product 1

HCID 684689472-Acetoxymethyl-3-methyl-4-propoxy-pyridineYield 111.2%

Procedure

To 20.3 g of 4-propoxy-2,3-dimethylpyridine-1-oxide, 44.0 g (4.0 eq.) of acetic anhydride was added, and the mixture was allowed to react for 4 hours at 90° C. Acetic anhydride was distilled off, and then the resulting concentrated residue was purified on a silica gel column, to obtain 27.8 g of 2-acetoxymethyl-3-methyl-4-propoxy-pyridine as an oily matter.

Workup

  1. customto react for 4 hours at 90° C
  2. distillationAcetic anhydride was distilled off
  3. customthe resulting concentrated residue was purified on a silica gel column

Sources & evidence

ORD record
ord-c203c1efd1c54484ab6c0daecdce4cf4
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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