反应详情

n-Butyl lithium (750 μL, 2M) was added methyl sulfoxide (6 mL) under argon at room temperature. The solution was stirred for half an hour, and (3-trimethylsillyl-2-propynyl)-triphenylphosphonium bromide (1 mmole) in methyl sulfoxide was added and stirred for one hour. 9-Oxo-nonanoic acid methyl ester in methyl sulfoxide was added to the reaction mixture and stirred for 4.5 hours. The reaction mixture was poured onto ice water and extracted with ethyl acetate three times. The organic layers were combined and dried to obtain crude mixture, which was further purified through Si gel column chromatography. The product contained trans and cis isomers in about 8:2 ratio.

1. stirringstirred for one hour
2. stirringstirred for 4.5 hours
3. additionThe reaction mixture was poured onto ice water
4. extractionextracted with ethyl acetate three times
5. customdried
6. customto obtain crude mixture, which
7. customwas further purified through Si gel column chromatography