Water → 1-methyl-2,3-dimethylene-8-oxa-bicyclo[3.2.1]octane
Reaction equation
C(OCC)C.O[CH:7]([CH2:13][C:14]([CH2:17][Si](C)(C)C)=[C:15]=[CH2:16])[CH2:8][CH2:9][C:10](=[O:12])[CH3:11].FC(F)(F)S(O[Si](C)(C)C)(=O)=O.O>C(OCC)(=O)C>[CH3:11][C:10]12[O:12][CH:7]([CH2:8][CH2:9]1)[CH2:13][C:14](=[CH2:17])[C:15]2=[CH2:16]Participants
Conditions
- Temperature
- -78 °C
Procedure
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%).
Workup
- stirringWhile stirring the reaction mixture
- temperaturethe reaction temperature was slowly increased to room temperature for 3 hours
- stirringThe reaction mixture was stirred at room temperature for 30 minutes
- stirringAfter stirring for about 5 minutes
- washwashed with water and saturated brine
- customThe organic layer was separated from the reaction mixture
- dry with materialdried with anhydrous magnesium sulfate (MgSO4)
- customThe solvent was removed under reduced pressure
- customthe remaining material was purified with column chromatography (EtOAc/n-hexane=1/5)
Sources & evidence
- ORD record
- ord-c9468fbfcecd4c3a9ebd4c328a36dce6
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094913B2
Reaction notes
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