66567-03-1Relevant academic research and scientific papers
Reduction of Diethyl Alkylidenemalonates and Ethyl Propylideneacetoacetate with Complex Metal Hydrides
Kuznetsov,Alekseeva,Gren'
, p. 396 - 399 (2007/10/03)
Reduction of diethyl alkylidenemalonates and ethyl propylideneacetoacetate with complex metal hydrides occurs at the olefinic moiety. The reduction with NaBH4 in t-BuOH-MeOH yields saturated 1,3-diols; LiAlH4 as reducing agent gives rise to corresponding saturated esters. With NaAlH4 in THF, a mixture of products is formed, which contains considerable amounts of the initial ester and low-boiling compounds; ethyl propylideneacetoacetate is also reduced to ethyl propylacetoacetate. The system NaBH4-AlBr3 in THF almost does not reduce diethyl isopropylidenemalonate, whereas under the same conditions ethyl propylideneacetoacetate is converted into ethyl 2-(1-hydroxyethyl)pentanoate.
