m-Chloroperbenzoic acid → 5-(methoxymethoxy)-2-neopentylpyridine-N-oxide

HRID 552796Notes

Reaction equation

HRID 552796 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:9][CH:10]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N+:9]([O-:24])[CH:10]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 575158425-(Methoxymethoxy)-2-neopentylpyridine

Product 1

HCID 671636565-(methoxymethoxy)-2-neopentylpyridine-N-oxideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Methoxymethoxy)-2-neopentylpyridine (11.0 g, 52.6 mmol) was dissolved in CH2Cl2 (200 mL) to which mCPBA (18.1 g, 105 mmol) was added, and the mixture was stirred under N2 for about 4 h. The mixture was quenched with 1M NaOH (200 mL) and stirring was continued vigorously for 10 min. The mixture was extracted with CH2Cl2 (2×200 mL), the combined organic layers were washed with saturated NaCl, dried (Na2SO4), and evaporated to give 5-(methoxymethoxy)-2-neopentylpyridine-N-oxide (11.8 g, 99.7% yield) as a brown oil which was used without purification in the next step.

Workup

  1. additionwas added
  2. customThe mixture was quenched with 1M NaOH (200 mL)
  3. stirringstirring
  4. waitwas continued vigorously for 10 min
  5. extractionThe mixture was extracted with CH2Cl2 (2×200 mL)
  6. washthe combined organic layers were washed with saturated NaCl
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-2b5b808fabcc4b459babf4ef4fa1730f
Source dataset
uspto-grants-2011_05
Patent number
US07951838B2

Reaction notes

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