Hydrogen Peroxide → HCID 56621154, compound

HRID 1789608Notes

Reaction equation

HRID 1789608 reaction equation
[CH2:1]([CH:5]1[C:9](=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:20])[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[OH:21]O.[H-].[Na+].[Cl-].[NH4+]>CO>[O:21]1[C:6]2[CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:9](=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:8](=[O:20])[C:7]1=2

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 56616807HCID 56616807, compound

Product 1

HCID 56621154HCID 56621154, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

660 mg (2.37 mmol) of 4-butyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 10 ml of methanol. With ice cooling and stirring, 1.2 ml of 30% aqueous hydrogen peroxide and then 0.23 ml of 1N sodium hydride were added to the solution and the mixture was stirred at 0° C. for 20 minutes. Saturated aqueous ammonium chloride was added thereto and was extracted with hexane. The organic layer was washed with a saturated saline solution, dried over sodium sulfate anhydride, filtered, concentrated, and chromatographed on a column of silica gel (silica gel, 30 g; eluent, hexane:ethyl acetate=10:1) to obtain 500 mg (yield 72%) of 2,3-epoxy-4-butyl-5-(6-methoxycarbonylhexylidene)cyclopentenone.

Workup

  1. stirringthe mixture was stirred at 0° C. for 20 minutes
  2. extractionwas extracted with hexane
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over sodium sulfate anhydride
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on a column of silica gel (silica gel, 30 g; eluent, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9a0fa21a3b5245a2a7bee1f86b762e6c
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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