Citric Acid → (RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

HRID 582738Notes

Reaction equation

HRID 582738 reaction equation
[CH2:1]([C:4]1[C:8](=[O:9])[CH2:7][CH:6]([OH:10])[CH:5]=1)[CH:2]=[CH2:3].N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Si:16]([O:10][CH:6]1[CH2:7][C:8](=[O:9])[C:4]([CH2:1][CH:2]=[CH2:3])=[CH:5]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 130378562-Cyclopenten-1-one, 4-hydroxy-2-(2-propenyl)-

Product 1

HCID 14189022(RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) etherYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution mixture of 8.8 g of (RS)-3-allyl-4-oxo-2-cyclopenten-1-ol, 100 ml of N,N-dimethylformamide and 4.75 g of imidazole was added t-butyldimethylsilyl chloride under ice-cooling, and the resulting mixture was stirred under ice-cooling for 8 hours. Then the reaction liquid was poured into ice-cooled 5% aqueous solution of citric acid and extracted two times with diethyl ether. The combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 13.1 g of (RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 81%

Workup

  1. temperaturecooling
  2. temperaturecooling for 8 hours
  3. customThen the reaction liquid
  4. additionwas poured into ice-
  5. extractionextracted two times with diethyl ether
  6. washThe combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-87c89e70055340dea3bf20d70c1fa45a
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

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