1,8-Diazabicyclo(5.4.0)undec-7-ene → 3a,7a-dihydro-2,2-dimethyl-1,3-Benzodioxole

HRID 2078029Notes

Reaction equation

HRID 2078029 reaction equation
Br[CH:2]1[CH:12](Br)[CH2:11][CH:5]2[O:6][C:7]([CH3:10])([CH3:9])[O:8][CH:4]2[CH2:3]1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH3:9][C:7]1([CH3:10])[O:6][CH:5]2[CH:11]=[CH:12][CH:2]=[CH:3][CH:4]2[O:8]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 128857685,6-Dibromo-2,2-dimethylhexahydro-2H-1,3-benzodioxole

Product 1

HCID 117687613a,7a-dihydro-2,2-dimethyl-1,3-Benzodioxole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound obtained in Step (11) was placed in a reaction vessel, and air in the vessel was replaced with nitrogen. After that, the compound was dissolved in dehydrated toluene (116 ml). Distilled DBU (6.0 ml, 40.1 mmol) was added to the solution, and the mixture was refluxed for 6 hours. After the reaction product had been filtrated, sodium hydrogen carbonate was added to the filtrate, and the organic layer was dried over magnesium sulfate, whereby 2,2-dimethyl-3a,7a-dihydrobenzo[1.3]dioxol was obtained. The compound was used in the next reaction without being further purified.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. filtrationAfter the reaction product had been filtrated
  3. additionsodium hydrogen carbonate was added to the filtrate
  4. dry with materialthe organic layer was dried over magnesium sulfate

Sources & evidence

ORD record
ord-f106c428679c43f78217743b87c6b20e
Source dataset
uspto-grants-2011_04
Patent number
US07928221B2

Reaction notes

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