Reaktion #1330389

Reaktionsgleichung

potassium carbonate

(1R,4S)-4-acetoxy-2-cyclopenten-1-ol

imidazole

tert-butyldimethylsilyl chloride

→

(+)-(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between ethyl acetate and water
2. 2
   SonstigeThe organic layer was collected
3. 3
   Trocknendried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated to a residue that
6. 6
   workup.DISSOLUTIONwas dissolved in methanol (approximately 45 mL)
7. 7
   workup.STIRRINGthe mixture stirred overnight
8. 8
   SonstigeThe reaction mixture was then partitioned between ethyl acetate and water
9. 9
   SonstigeThe organic layer was collected
10. 10
    Trocknendried over sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated to a residue that
13. 13
    Sonstigewas purified by silica gel column chromatography with a 0–30% diethyl ether in hexanes gradient

Vorschrift

To a solution of (1R,4S)-4-acetoxy-2-cyclopenten-1-ol (1.0 g, 7.03 mmol) (Fluka) and imidazole (960 mg, 14.06 mmol) (Aldrich) in tetrahydrofuran (65 mL) at 0° C. was added tert-butyldimethylsilyl chloride (1.27 g, 8.44 mmol) (Aldrich). The mixture was allowed to warm slowly to room temperature, stirred overnight and then partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was dissolved in methanol (approximately 45 mL). To this solution was added potassium carbonate (1.17 g, 8.44 mmol) and the mixture stirred overnight. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was purified by silica gel column chromatography with a 0–30% diethyl ether in hexanes gradient to give (+)-(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol as a colorless oil. (Yield 1.43 g, 95%).

Quelle