Hydrogen Peroxide → HCID 56614884, compound

HRID 1789614Notes

Reaction equation

HRID 1789614 reaction equation
[CH:1]([C@H:9]1[C:13](=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:12](=[O:24])[CH:11]=[CH:10]1)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:25]O.[Cl-].[NH4+]>CO.[OH-].[Na+]>[O:25]1[C:10]2[C@@H:9]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:13](=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:12](=[O:24])[C:11]1=2

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 25517Ammonium ChlorideHCID 54540710HCID 54540710, compound

Product 1

HCID 56614884HCID 56614884, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 600 mg (1.8 mmol) of (4R)-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone in 6 ml of methanol was added 0.92 ml (9.0 mmol) of 30% aqueous hydrogen peroxide with ice cooling and stirring, and then 60 microliters (60 micromol) of 1N aqueous sodium hydroxide was added. The mixture was stirred at 0 C. for 45 minutes. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with hexane. The organic layer was washed with a saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated and subjected to silica gel column chromatography (silica gel, 40 g; eluent, hexane:ethyl acetate=10:1→5:1) to give 491 mg (yield 78%) of (4S)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxycarbonyl-hexylidene)cyclopentenone.

Workup

  1. stirringThe mixture was stirred at 0 C
  2. extractionthe mixture was extracted with hexane
  3. washThe organic layer was washed with a saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c2d48a2dec08485ab4d3d3bc6d7e1aee
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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