High yield synthesis of α propargylic acrylic ester : A general access to α substituted acrylic esters

Synthetic Communications

Volumn 18, Issue 11, 1988, Pages 1213-1223

  Queignec, Rene ^a   Kirschleger, Bernard ^a   Lambert, Francois ^a   Aboutaj, Mohcomed ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001177310     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397918808060913     Document Type: Article

References (9)

1. Kirschleger B., Queignec R., Synthesis 1986, 927.
2. Ravikuman V.T., Thangaraj K., Swaminathan S., Rajagapalan K., Synthesis 1985, 985 and references cited therein.
3. The same reaction with ethyl acetylacetate gives 10% of dipropargylated product, see Kirschleger B., Queignec R., C.R. Acad. Sci. 1985, 301, 2, 143.
4. Tsuboi S., Uno T., Takeda A., Chem. Lett. 1978, 1325.
5. Ueno Y., Setai H., Okavara M., Tetrahedron Lett. 1978, 3753.
6. A limitation has been found in a attempt to synthesise the homologous β and α substituted acrylate esters because aldehydes and ketones are unreactive towards the monosubstituted keto ester anion.
7. See reference 1 and references cited therein; Miller R.B., Smith B.F., Synth. Comm. 1973, 3, 359; Marino J.P., Floyd D.M., J. Am. Chem. Soc., 1974, 96, 7138.
8. Marino J.P., Floyd D.M., J. Am. Chem. Soc., 1974, 96, 7138.
9. Ethylbenzoylacetate slighty decomposes in the light giving acetophenone as a by-product. It must be stored in the refrigerator or in the dark.