1,8-Diazabicyclo(5.4.0)undec-7-ene → {[1-(2,4-Dichlorophenyl)vinyl]sulfonyl}benzene

HRID 1297502Notes

Reaction equation

HRID 1297502 reaction equation
C1CCN2C(=NCCC2)CC1.C(O[CH2:16][CH:17]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34])[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])(=O)C>C1COCC1>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[C:17]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[CH2:16]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 589147942-(2,4-Dichlorophenyl)-2-(phenylsulfonyl)ethyl acetate

Product 1

HCID 58914799{[1-(2,4-Dichlorophenyl)vinyl]sulfonyl}benzeneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

DBU (1.5 eq) in THF was added to a solution of 2-(2,4-dichlorophenyl)-2-(phenylsulfonyl)ethyl acetate (3) (1 eq) in THF at rt. After stirring for 40 min., the reaction was quenched with sat. aq. NH4Cl. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to give the {[1-(2,4-dichlorophenyl)vinyl]sulfonyl}benzene (4) (97% yield).

Workup

  1. customthe reaction was quenched with sat. aq. NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c7cc023e0d64bf1b451a38306f0d605
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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