Reaktion #10997

Reaktionsgleichung

H2O

diethyl ether

5-hydroxy-7-trimethylsilanylmethyl-nona-7,8-diene-2-one

trimethylsilyl trifluoromethanesulfonate

→

product

Ausbeute 94.3%

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

Ausbeute 94.3%

Lösungsmittel

ethyl acetate

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 magnesium sulfate (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 5-hydroxy-7-trimethylsilanylmethyl-nona-7,8-diene-2-one (86 mg, 0.36 mmol) under nitrogen atmosphere. While stirring at −78° C., trimethylsilyl trifluoromethanesulfonate (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 ethyl acetate (EtOAc) and washed with water and saturated brine. The organic layer was separated from the reaction mixture and dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed under reduced pressure and the remaining material was purified with column chromatography (EtOAc/n-hexane=1/5) to obtain 51 mg of the product (94%).

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