Citric Acid → HCID 22908403, compound

HRID 1379943Notes

Reaction equation

HRID 1379943 reaction equation
N1[CH:5]=[CH:4]N=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[C:14](O)(=O)[CH2:15][C:16]([CH2:21][C:22]([OH:24])=O)(C(O)=O)[OH:17].[CH3:27]N(C)C=O>>[Si:10]([O:24][CH:22]1[CH2:21][C:16](=[O:17])[C:15]([CH2:14][CH3:27])=[C:4]1[CH3:5])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 22908403HCID 22908403, compoundYield 82%

Procedure

After 10 g of(RS)-4-hydroxy-3-methyl-2-ethylcyclopent-2-en-1-one and 5.78 g of imidazole were dissolved in 100 ml of dry dimethylformamide, 11.91 g of t-butyldimethylchlorosilane was added to the solution at an ambient temperature. After stirring at an ambient temperature for 14 hours, the reaction solution was added to 5% aqueous citric acid under ice-water cooling, and extracted three times with diethyl ether. The combined organic layer was washed successively with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography to yield 14.231 g of (RS)-4-t-butyldimethylsilyloxy-3-methyl-2-ethylcyclopent-2-en-1-one. Yield 82% (Eluent: n-hexane/ethyl acetate=5/1 (v/v))

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic layer was washed successively with a saturated sodium hydrogencarbonate solution
  3. dry with materiala saturated sodium chloride solution, and dried with anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-076afa651a7d45fd8d48ef1b5d43170e
Source dataset
uspto-grants-1997_09
Patent number
US05672779

Reaction notes

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