Cyanoethanoate esters, acidity

A variety of nucleophilic agents can be used propanedinitrile, 3-oxo-butanoate esters, and cyanoethanoate esters all form relatively stable car-banions and function well in Michael addition reactions. Obviously, if the carbanion is too stable, it will have little or no tendency to attack the double bond of the a./8-unsaturated acid derivative. The utility of the Michael addition for preparing 1,5-dicarbonyl compounds is illustrated by the examples in Exercise 18-49. 

Ethyl Cyanoacetate. Cyaitoacetic acid ethyl estert cyanoacetic ester ethyl cyanoethanoate malonic acid ethyl ester nitrile. CsH,N02 mol wt 113.12. C 53.09%. H 6.24%, N 12.39%, O 28.29%. CNCH2COOC2HS. Made by the interaction of sodium cyanide and chloroacetic acid and subsequent esterification of the cyanoacetic acid formed Kob -ler, Allen. Org. Syn. 3, 53 (1923) Inglis, ibid. 8, 74 (1928). 

SYNS CYANACETATE ETHYLE (GERMAN) CYANOACETIC ACID ETHYL ESTER CYANOACETIC ESTER ESTERE CIANOACETICO ETHYL CYANOACETATE ETHYL CYANOETHANOATE ETHYLESTER KYSEUNY KYANOCTOVE MALONIC ACID ETHYL ESTER NITRILE USAF KF-25... 

Beilstein Handbook Reference) Acetic acid, cyano-, ethyl ester AI3-19027 BRN 0605871 Cyanacetate ethyle Cyanoacetic acid ethyl ester Cyanoacetic ester EINECS 203-309-0 Estere cianoacetico Ethyl cyanacetate Ethyl cyanoacetate Ethyl cyanoethanoate Ethylester kyseliny kyanoctove HSDB 2769 Malonic acid ethyl ester nitrile NSC 8844 UN2666 USAF KF-25. Liquid mp = -22.5° bp = 205° d = 1.0654 very soluble in EtOH, Et20. 

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