Reaktion #10998

Reaktionsgleichung

H2O

diethyl ether

4-hydroxy-1-phenyl-6-trimethylsilanylmethyl-octa-6.7-diene-1-one

TMSOTf

→

product

Ausbeute 96.8%

2,3-dimethylene-1-phenyl-8-oxa-bicyclo[3.2.1]octane

Ausbeute 96.8%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGWhile stirring the reaction mixture
2. 2
   Temperaturthe reaction temperature was slowly increased to room temperature for 3 hours
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 30 minutes
4. 4
   workup.STIRRINGAfter stirring for about 5 minutes
5. 5
   Waschenwashed with water and saturated brine
6. 6
   SonstigeThe organic layer was separated from the reaction mixture
7. 7
   Trocknendried with anhydrous MgSO4
8. 8
   SonstigeThe solvent was removed under reduced pressure
9. 9
   Sonstigethe remaining material was purified with column chromatography (EtOAc/n-hexane=1/5)

Vorschrift

1.50 mL of diethyl ether was added to 4-hydroxy-1-phenyl-6-trimethylsilanylmethyl-octa-6.7-diene-1-one (110 mg, 0.36 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (64.7 μL, 0.36 mmol) was added. While stirring the reaction mixture, the reaction temperature was slowly increased to room temperature for 3 hours. The reaction mixture was stirred at room temperature for 30 minutes. After the reaction was completed, H2O was added. After stirring for about 5 minutes, the reaction mixture was diluted with EtOAc and washed with water and saturated brine. The organic layer was separated from the reaction mixture and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the remaining material was purified with column chromatography (EtOAc/n-hexane=1/5) to obtain 74 mg of the product (96%).

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