1,4-Dichloro-2-butene, (2E)- → 1-Phenylsulfonyl-1-acetyl-2-vinylcyclopropane
Reaction equation
[C:1]1([S:7]([CH2:10][C:11](=[O:13])[CH3:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14](Cl)/[CH:15]=[CH:16]/[CH2:17]Cl>>[C:1]1([S:7]([C:10]2([C:11](=[O:13])[CH3:12])[CH2:17][CH:16]2[CH:15]=[CH2:14])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
Utilizing a phase-transfer procedure similar to that described in Example I, phenylsulfonylacetone was reacted with 1,4-dichlorobutene-2 to obtain 1-phenylsulfonyl-1-acetyl-2-vinylcyclopropane. For the reaction, 9.91 grams phenylsulfonylacetone (Parish Chemical Co.) and 6.25 grams 1,4-dichlorobutene-2 were combined in 20 mls sulfolane containing 6.6 grams potassium hydroxide (85%) and 5 mole percent tricaprylylmethylammonium chloride. The reaction mixture was stirred at 35°-40° C. for 31/2 hours. One-hundred mls water was then added to dissolve the white granular precipitate which had formed and the mixture extracted several times with ether. A crude red oil (10.8 grams) was obtained after removal of the ether and further work-up utilizing a Waters Preparatory Liquid Chromatograph 500A equipped with a gel permeation column and operated at a flow rate of 0.1 l/min yielded the cis and trans isomers of 1-phenylsulfonyl-1-acetyl-2-vinylcyclopropane. ##STR18## trans 1-phenylsulfonyl-1-acetyl-2-vinylcyclopropane
Sources & evidence
- ORD record
- ord-751477902f794577865dca0d090f3ea1
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04522950
Reaction notes
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