Methanol → [5-(1-Methylethoxy)pyridin-2-yl]methyl acetate

HRID 1038539Notes

Reaction equation

HRID 1038539 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:12])=[N+:9]([O-])[CH:10]=1)[CH3:3].CO.[C:15]([O:18]C(=O)C)(=[O:17])[CH3:16]>>[C:15]([O:18][CH2:12][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[CH:10][N:9]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 665980675-(1-Methylethoxy)-2-methylpyridine 1-oxide

Product 1

HCID 66598252[5-(1-Methylethoxy)pyridin-2-yl]methyl acetateYield 71%

Conditions

Temperature
140 °C

Procedure

5-(1-methylethoxy)-2-methylpyridine 1-oxide (234 mg, 1.40 mmol) was dissolved in acetic anhydride (3.0 mL), and the mixture was stirred at 140° C. for 1 hour. At room temperature, the reaction solution was added methanol, stirred, concentrated in vacuo, and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium hydrogen carbonate and brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate) and [5-(1-methylethoxy)pyridin-2-yl]methyl acetate (209 mg (yield 71%)) was obtained as a yellow oil.

Workup

  1. stirringstirred
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-12c7b8ac6b1c4389ac69f5d2f234449d
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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