Citric Acid → HCID 19428659, compound

HRID 1078999Notes

Reaction equation

HRID 1078999 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH:9]=[CH2:10])=[C:3]1[CH3:11].N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Si:21]([O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH:9]=[CH2:10])=[C:3]1[CH3:11])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-HCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 19428659HCID 19428659, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 (RS)-4-hydroxy-3-methyl-2-(2-propenyl)-cyclopent-2-ene-1-one (5.0 g) and imidazole (2.91 g) were dissolved in dry dimethylformamide (20 ml), and tert-butyldimethylchlorosilane (5.45 g) was added thereto at room temperature and the resulting mixture was allowed to react for 14 hours at room temperature. The reaction solution was poured into an ice-cooled aqueous citric acid solution, and extracted three times with diethyl ether. The organic layers were combined, and the combined layer was washed with saturated aqueous sodium bicarbonate solution and brine in sequence, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resultant residue was subjected to column chromatography (eluent; n-hexane: ethy acetate=4:1) to afford (RS)-4-tert-butyldimethylsilyloxy-3-methyl-2-(2-propenyl)cyclopent-2-ene-1-one (8.48 g, yield 97.0%) as a pale yellow oil.

Workup

  1. customat room temperature
  2. customto react for 14 hours at room temperature
  3. extractionextracted three times with diethyl ether
  4. washthe combined layer was washed with saturated aqueous sodium bicarbonate solution and brine in sequence
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cd56f673a3b64e459ad5acb7d234730b
Source dataset
uspto-grants-1996_08
Patent number
US05550260

Reaction notes

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