Ethers. -The influence of the reaction conditions on the product ratios for the enol ether formation of various ketones with (II) is studied. -(FATAFTAH*, Z. A.; SAWALHAH, M.; RAWASHDEH, A. M.; Synth. Commun. 36 (2006) 22-24, 3655-3665; Dep. Chem., Yarmouk Univ., Irbid, Jordan; Eng.) -M. Bohle 18-161
The propargyloxydimethylsilyl enol ethers derived from propanone, 2-butanone, 3,3-dimethyl-2-butanone, 3-pentanone, 4-methyl-2-pentanone, 2-heptanone, 4-heptanone, 2,6-dimethyl-4-heptanone, cyclopentanone, cyclohexanone, cycloheptanone, benzophenone, and propiophenone have been synthesized by two methods: The thermodynamic method is conducted by heating the propargyloxysilyl chloride, triethylamine, and the corresponding ketone in acetonitrile at 40-508C for less than an hour in the presence of an equimolar amount of sodium iodide; the mixture is maintained at that temperature for an hour. The yields were in the range of 50-95%. In method two (kinetic controlled), lithium diisopropylamide (LDA) was used as a base to abstract the acidic hydrogen, and then the resulted enolate was quenched with silyl chloride, with lower yields than the previous method. NMR, IR, and elemental analysis were used to characterize the products. Some reactions of these compounds have been investigated.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.