Hydrogen Peroxide → HCID 86602486, compound

HRID 2247566Notes

Reaction equation

HRID 2247566 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]=[CH:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[OH:14].[K+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.C(#N)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH:11]3[CH:10]([O:14]3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 516893Potassium BicarbonateHCID 53350019HCID 53350019, compound

Product 1

HCID 86602486HCID 86602486, compoundYield 22.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (5 mL) solution of 1-(4-fluorophenyl)-2,5-dihydro-1H-pyrrole (300 mg) synthesized according to the method described in The Journal of Organic Chemistry vol. 25, p. 2230, 1960, acetonitrile (0.8 mL), potassium hydrogen carbonate (221 mg) and 20% hydrogen peroxide (0.8 mL) were added one by one, and the reaction solution was agitated at room temperature for 10 hours. Ethyl acetate and saturated sodium thiosulfate solution were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated sodium bicarbonate water, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 75 mg of the title compound was obtained by purifying the residue by silica gel chromatography (heptane: elution solvent; ethyl acetate=3:1). The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated sodium bicarbonate water, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bfda9ee12bd4f48af8009e50feb052a
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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