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

HRID 2242024Notes

Reaction equation

HRID 2242024 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-bbd09c414f0945c89842316ddc7544ca
Source dataset
uspto-grants-2010_03
Patent number
US07671049B2

Reaction notes

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