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

HRID 1038538Notes

Reaction equation

HRID 1038538 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.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 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), added 3-chloroperoxybenzoic acid (408 mg, 0.733 mmol) under ice-cold conditions, and the mixture was stirred at 0° C. for 45 minutes. The reaction solution was added ethyl acetate, saturated aqueous solution of sodium metabisulfite, and an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by 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. extractionan aqueous solution of sodium hydrogen carbonate, and 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 by silica-gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7fc0ce1ca0e448d1bdbc9ed53e4d1bbd
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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