trans-1,2-Bis(phenylsulfonyl)ethylene → 10,11-Bis(phenylsulfonyl)-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.2.02.6]undec-8-ene

HRID 244301Notes

Reaction equation

HRID 244301 reaction equation
[C:1]1([S:7](/[CH:10]=[CH:11]/[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1([CH3:31])[O:26][CH:25]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:24]2[O:23]1>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH:10]2[CH:11]([S:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH:30]3[CH:29]=[CH:28][CH:27]2[CH:25]2[CH:24]3[O:23][C:22]([CH3:31])([CH3:21])[O:26]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 5367099trans-1,2-Bis(phenylsulfonyl)ethyleneHCID 117687613a,7a-dihydro-2,2-dimethyl-1,3-Benzodioxole

Product 1

HCID 5842789810,11-Bis(phenylsulfonyl)-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.2.02.6]undec-8-ene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trans-1,2-bis(phenylsulfonyl)ethylene (1.37 g, 4.45 mmol) was added to a solution of the compound obtained in Step (12) in toluene, and air in a vessel containing the mixture was replaced with nitrogen. After having been refluxed for 8 hours, the mixture was concentrated under reduced pressure. The resultant reaction product was purified by silica gel chromatography (50% EtOAc/Hexane), whereby 10,11-bis(phenylsulfonyl)-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.2.02.6]undec-8-ene was obtained (2.0 g, 98%).

Workup

  1. additioncontaining the mixture
  2. temperatureAfter having been refluxed for 8 hours
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe resultant reaction product
  5. customwas purified by silica gel chromatography (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-7c8bc27a6374426881938a7721aefc7f
Source dataset
uspto-grants-2014_02
Patent number
US08658459B2

Reaction notes

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