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