Water → HCID 20158393, compound

HRID 986323Notes

Reaction equation

HRID 986323 reaction equation
[OH2:1].[OH2:2].O.[F-].[CH2:5]([N+](CCCC)(CCCC)CCCC)CCC.[Cl-:22].[NH4+].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[NH+]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.O.O1[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C)C=O>[Cl:22][C:35]1[C:36](=[O:2])[CH2:37][C:38]([CH2:47][CH2:48][CH:49]([CH3:50])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:44])[CH3:5])([OH:1])[CH:34]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724130Cornforth reagentHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 20158393HCID 20158393, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of 3-t-butyldimethylsilyloxy-2-chloro-5-(3,7-dimethyloctyl)-5-hydroxycyclopentene obtained in (1) above was dissolved in 1 ml of tetrahydrofuran, and 200 mg of tetrabutyl ammonium fluoride trihydrate was added. The mixture was stirred for 4 hours. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration and concentration, 30 mg of a crude product of 1-chloro-3(3,7-dimethyloctyl)-3,5-dihydroxycyclopentene was obtained. The crude product was dissolved in 1 ml of dimethylformamide, and 100 mg of pyridinium dichromate was added. The mixture was stirred for 2 hours. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqeuous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was chromatographed on a silica gel column to give 14 mg (yield 40%) of 2-chloro-4 -(3,7-dimethyloctyl)-4-hydroxy-2-cyclopentenone.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration, 30 mg of a crude product of 1-chloro-3(3,7-dimethyloctyl)-3,5-dihydroxycyclopentene
  5. customwas obtained
  6. stirringThe mixture was stirred for 2 hours
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with an aqeuous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration and concentration
  11. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-b346f30b0fcb4f3889b4376f72fee92e
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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