m-Chloroperbenzoic acid → HCID 68670205, compound

HRID 2071087Notes

Reaction equation

HRID 2071087 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:10]([CH3:12])=[CH2:11])[CH:9]=1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:5]=[N+:6]([O-:23])[CH:7]=[C:8]([C:10]([CH3:12])=[CH2:11])[CH:9]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68670854HCID 68670854, compound

Product 1

HCID 68670205HCID 68670205, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(dimethoxymethyl)-5-(prop-1-en-2-yl)pyridine (178 mg, 0.92 mmol) in CH2Cl2 (10 mL) was added m-CPBA (227 mg, 1.0 mmol). The reaction mixture was stirred for 2 h and quenched with saturated aqueous NaHCO3. The layers were separated and the organic layer was washed with brine and dried over Na2SO4. The solvent was removed to provide 3-(dimethoxymethyl)-5-(prop-1-en-2-yl)pyridine 1-oxide (209 mg), which was converted to 3-formyl-5-(prop-1-en-2-yl)pyridine 1-oxide as described herein.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-ea40c77c2b664f0aa4e5de5180106e7b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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