Hydrochloric Acid → HCID 56626017, compound

HRID 1789619Notes

Reaction equation

HRID 1789619 reaction equation
OO.[OH:3][CH:4]([CH2:23][CH:24]([CH3:29])[CH2:25][CH2:26][CH2:27][CH3:28])[CH:5]=[CH:6][CH:7]1[C:11](=[CH:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])[C:10](=[O:22])[CH:9]=[CH:8]1.[OH-].[Na+].[Cl-:32].[NH4+].Cl.C(=O)([O-])O.[Na+]>CO.CC(C)=O>[Cl:32][C:9]1[C:10](=[O:22])[C:11](=[CH:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])[CH:7]([CH:6]=[CH:5][CH:4]([OH:3])[CH2:23][CH:24]([CH3:29])[CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 56613281HCID 56613281, compound

Product 1

HCID 56626017HCID 56626017, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

0.3 ml of 30% aqueous hydrogen peroxide was added to a solution of 160 mg (428 micromol) of 4-(3-hydroxy-5-methyl-1nonenyl)-5-(6-methoxycarbonyl-5-hexenylidene)-2-cyclopentenone in 5 ml of methanol under ice cooling and stirring, and then 60 microliters of 1N sodium hydroxide was added. The mixture was stirred at 0° C. for 20 minutes. A saturated aqueous solution of ammonium chloride was added, and the mixtue was extracted with hexane. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered and concentrated to give an oily product. The product was dissolved in 3 ml of acetone, and 0.5 ml of concentrated hydrochloric acid was added. The mixture was stirred for 50 minutes. A saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with ethylacetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel, 10 g; eluent, cyclohexane:ethylacetate=4:1) to give 82 mg (yield 47%) of 2-chloro-4-(3-hydroxy-5-methyl-1-nonenyl)-5-(6-methoxycarbonyl-5-hexenylidene)-2-cyclopentenone.

Workup

  1. stirringThe mixture was stirred at 0° C. for 20 minutes
  2. extractionthe mixtue was extracted with hexane
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe dried product was filtered
  6. concentrationconcentrated
  7. customto give an oily product
  8. stirringThe mixture was stirred for 50 minutes
  9. extractionthe mixture was extracted with ethylacetate
  10. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationThe dried product was filtered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-47fd1f1e35484868b03f80f53d8b1bfc
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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