Water → 10,11-Dimethylene-12-oxa-tricyclo[6.3.1.01,6]dodecane

HRID 10905Notes

Reaction equation

C(OCC)C.O[CH:7]([CH2:16][C:17]([CH2:20][Si](C)(C)C)=[C:18]=[CH2:19])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.O>CCOC(C)=O>[CH2:20]=[C:17]1[C:18](=[CH2:19])[C:10]23[O:15][CH:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:16]1

Participants

Conditions

Temperature: -78 °C

Procedure

1.5 mL of diethyl ether was added to 2-(2-hydroxy-4-trimethylsilanylmethyl-hexa-4,5-dienyl)-cyclohexanone (100 mg, 0.36 mmol) under nitrogen atmosphere. While stirring at −78° C., TMSOTf (64.5 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=1/6) to obtain 53 mg of the product (78%).

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 MgSO4
customThe solvent was removed under reduced pressure
customthe remaining material was purified with column chromatography (EtOAc/n-hexane=1/6)

Sources & evidence

ORD record: ord-64eff3d1816e4a43a31ba2f5a16e85bb
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094913B2

Reaction notes

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