Procedures for the Acylation of Diethyl Malonate and Ethyl Acetoacetate with Acid Chlorides Using Tertiary Amine Bases and Magnesium Chloride

Journal of Organic Chemistry

Volumn 50, Issue 15, 1985, Pages 2622-2624

  Rathke, Michael W ^a   Cowan, Patrick J ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845377839     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00215a003     Document Type: Article

References (6)

1. Dow Summer Fellow, 1983.
2. For leading references, see House, H. O. “Modern Synthetic Reactions”; Benjamin/Cummings Publishing Co.: Reading, MA, 1972; pp 635–665.
3. Oikawa, Y.; Sugano, K.; Yonemitso, O. J. Org. Chem. 1978, 43, 2087.
4. For a general discussion of acidity enhancement by metal complexation see: Houghton, R. P. “Metal Complexes in Organic Chemistry”; Cambridge University Press: London, 1979; pp 114–116. For a recent application of the principal to β-keto phosphonate reactions using LiCl see: Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183. Howden, M. E. H.; Tyler, M. Tetrahedron Lett. 1975, 24, 1979.
5. (a) Tarbell, D. S.; Price, J. A. J. Org. Chem. 1957, 22, 245. (b) Viscontini, M.; Merckling, N. Helv. Chim. Acta 1952, 35, 2280. (c) Reynolds, G. A.; Hauser, C. R. “Organic Syntheses”; Wiley: New York, 1963; Collect. Vol. 4, p 708.
6. Pray, A. R. “Inorganic Synthesis”; Wiley: New York, 1973; Collect. Vol. 5, pp 153–6.