Ethyl Acetate → 3,5-Dimethylpyridin-1-ium-1-olate

HRID 2172877Notes

Reaction equation

HRID 2172877 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1.CCOC(C)=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 115653,5-DimethylpyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 194853,5-Dimethylpyridin-1-ium-1-olateYield 93.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3,5-dimethylpyridine (85 g, 0.8 mol) in CHCl3 (1500 mL) was added m-CPBA (180 g, 0.88 mol) in portions at 0° C. Then the mixture was stirred at room temperature for 18 hr. TLC (petroleum ether:EtOAc=1:1) showed the starting material was consumed almost. After diluting with CH2Cl2 (1200 mL), the solution was washed with Na2S2O3(aq.) (600 mL), NaHCO3(aq.) (600 mL) and brine (600 mL). The resulting material was dried over Na2SO4 and concentrated in vacuo to give crude material which was purified by chromatography on silica gel with EtOAc:CH2Cl2=4:1 to afford 3,5-dimethylpyridine 1-oxide (92 g, 93%) as light yellow solid.

Workup

  1. customwas consumed almost
  2. additionAfter diluting with CH2Cl2 (1200 mL)
  3. washthe solution was washed with Na2S2O3(aq.) (600 mL), NaHCO3(aq.) (600 mL) and brine (600 mL)
  4. dry with materialThe resulting material was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give crude material which
  7. customwas purified by chromatography on silica gel with EtOAc

Sources & evidence

ORD record
ord-2889ed5301794002942833fbd0727135
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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