Citric Acid → (RS)-4-t-butyldimethylsilyloxy-3-methyl-2-(2,2,2-trifluoroethyl)cyclopent-2-en-1-one

HRID 1379944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379944
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]([F:12])([F:11])[F:10])=[C:3]1[CH3:13].N1C=CN=C1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Si:23]([O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]([F:10])([F:11])[F:12])=[C:3]1[CH3:13])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22283798(RS)-2-methyl-3-(2,2,2-trifluoroethyl)-4-oxocyclopent-2-en-1-ol

Produkt 1

HCID 22908402(RS)-4-t-butyldimethylsilyloxy-3-methyl-2-(2,2,2-trifluoroethyl)cyclopent-2-en-1-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

After 10 g of (RS)-4-hydroxy-3-methyl-2-(2,2,2-trifluoroethyl)cyclopent-2-en-1-one and 4.2 g of imidazole were dissolved in 100 ml of dry dimethylformamide, 8.54 g of t-butyldimethylchlorosilane was added to the solution at an ambient temperature. After stirring at an ambient temperature for 12 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 14.3 g of (RS)-4-t-butyldimethylsilyloxy-3-methyl-2-(2,2,2-trifluoroethyl)cyclopent-2-en-1-one. Yield 90% (Eluent: n-hexane/ethyl acetate=5/1 (v/v))

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-96b0dc9639b64652989dbe9595cc6175
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672779

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