Ethyl Acetate → 5-(1-Methylethoxy)-2-methylpyridine 1-oxide

HRID 1690168Notes

Reaction equation

HRID 1690168 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1)[CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:17].C(OCC)(=O)C>ClCCl>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[N+:9]([O-:17])[CH:10]=1)[CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 13339809Pyridine, 2-methyl-5-(1-methylethoxy)-

Product 1

HCID 665980675-(1-Methylethoxy)-2-methylpyridine 1-oxideYield 217.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(1-Methylethoxy)-2-methylpyridine (227 mg, 0.661 mmol) was dissolved in dichloromethane (7.5 mL). The resultant mixture was added with 3-chloroperoxybenzoic acid (408 mg, 0.733 mmol) under ice-cold conditions, and stirred at 0° C. for 45 minutes. The reaction solution was added with ethyl acetate, a saturated aqueous solution of sodium metabisulfite, and an aqueous solution of sodium hydrogen carbonate, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (ethyl acetate) and 5-(1-methylethoxy)-2-methylpyridine 1-oxide (240 mg, yield 6%) was obtained as a colorless oil.

Workup

  1. extractiona saturated aqueous solution of sodium metabisulfite, and an aqueous solution of sodium hydrogen carbonate, and then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-3c5bb8aa9cf04039aa2b2b345f9e16cd
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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