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

HRID 1690169Notes

Reaction equation

HRID 1690169 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%

Procedure

5-(1-Methylethoxy)-2-methylpyridine 1-oxide (234 mg, 1.40 mmol) was dissolved in acetic anhydride (3.0 mL) and the resultant mixture was stirred at 140° C. for 1 hour. The reaction solution was added with methanol at room temperature, stirred, then 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 using 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. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous solution of sodium hydrogen carbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-bc6f73da320441c6be04896e1bcbe649
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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