Synthesis of dimethylvinylsilyloxyalkenes from aldehydes and ketones

Abstract EN

Chlorodimethylvinylsilane is reacted with an equivalent amount of ketone or aldehyde enolates.

obtained from deprotonation of 3-pentanone, 3,3-dimethyl-2-butanone.

acetophenone, propiophenone, cyclopentanone, cyclohexanone.

cyclohep-tanone, pentanal, hexanal and heptanal.

to give dimethylvinylsilyloxyalkenes in good yields.

Triethylamine as well as lithium diisopropylamide (LDA) are used in deprotonation of aldehydes and ketones.

Acetophenone and 3,3-dimethyl-2-bulanone give low yields with triethylamine and the aldehydes give poor yields with LDA.

The acid- and base -catalyzed rate of hydrolysis of 1 was examined.

All products have been characterized on the basis of their NMR, IR and elemental analysis data.