Synthesis of some allyldimethylsilyl enol ethers derived from ketones

Abstract EN

Allyldimethylsilyl enol ethers, derived from acetone 3-pentanone, 3,3-dimethyl, 2-butanone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone and propi-ophenone have been synthesized by refluxing the mixture of triethylamine allyldime-thylchlorosilane and the corresponding ketone in dimethylformamide for 18-48 h.

The yields are in the range of 61-94%.

Alternatively, a stronger base lethium diisopropyla-mide (LDA) is used for deprotonation of the above mentioned ketones at 0°C.

The eno-lates are then quenched with allyldimethylchlorosilane.

The yields are very good (65-100%).

The allydimethylsilyl enol ethers have been characterized on the basis of their NMR, IR, and elemental analysis data.