Hydrogen Peroxide → 5-(methoxymethoxy)-2-methylpyridin-4(1H)-one

HRID 1038589Notes

Reaction equation

HRID 1038589 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6](B(O)O)=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1.OO.S(OOS([O-])(=O)=O)([O-])(=O)=[O:18].[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6](=[O:18])[CH:7]=[C:8]([CH3:11])[NH:9][CH:10]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 62655Sodium PersulfateHCID 66598330[5-(Methoxymethoxy)-2-methylpyridin-4-yl]boronic acid

Product 1

HCID 665984905-(methoxymethoxy)-2-methylpyridin-4(1H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(methoxymethoxy)-2-methylpyridin-4-ylboronic acid (500 mg, 2.54 mmol) in tetrahydrofuran (12.7 mL), an aqueous solution of hydrogen peroxide (purity 30%) (2.9 mL, 25.4 mmol) was added at room temperature, and the mixture was stirred at room temperature for 4 hours. The reaction solution was added a saturated aqueous solution of sodium persulfate, and concentrated in vacuo. The obtained residue was washed and filtered with chloroform/methanol, and the title compound (440 mg (yield >100%)) was obtained as a yellow amorphous.

Workup

  1. concentrationconcentrated in vacuo
  2. washThe obtained residue was washed
  3. filtrationfiltered with chloroform/methanol

Sources & evidence

ORD record
ord-b49f6aaf458c4c978144c34ec74e01ab
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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