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Condensation of Diethyl Malonate with Methyl Vinyl Ketone

Publication ,  Journal Article
Spencer, TA; Newton, MD; Baldwin, SW
Published in: Journal of Organic Chemistry
April 1, 1964
Published version (DOI)

Ethoxide-catalyzed reaction of diethyl malonate with methyl vinyl ketone yields 1-carboxy-6-methylbicyclo-[3.3.1]non-6-ene-2,4-dione (VI) and, after hydrolysis, 1-methyl-2-acetyl-4-carboxycyclohexene-1 (XI). The separately prepared mono-Michael adduct (V) can be cyclized in very good yield to a mixture of 4-carboethoxycyclohexane-1,3-dione (II) and 3-ethoxy-6-carboethoxy-Δ2-cyclohexenone (XIII). © 1964, American Chemical Society. All rights reserved.

Duke Scholars

Steven W. Baldwin
Author Steven W. Baldwin Chemistry
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Published In

Journal of Organic Chemistry

DOI

10.1021/jo01027a004

EISSN

1520-6904

ISSN

0022-3263

Publication Date

April 1, 1964

Volume

29

Issue

4

Start / End Page

787 / 789

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Spencer, T. A., Newton, M. D., & Baldwin, S. W. (1964). Condensation of Diethyl Malonate with Methyl Vinyl Ketone. Journal of Organic Chemistry, 29(4), 787–789. https://doi.org/10.1021/jo01027a004
Spencer, T. A., M. D. Newton, and S. W. Baldwin. “Condensation of Diethyl Malonate with Methyl Vinyl Ketone.” Journal of Organic Chemistry 29, no. 4 (April 1, 1964): 787–89. https://doi.org/10.1021/jo01027a004.
Spencer TA, Newton MD, Baldwin SW. Condensation of Diethyl Malonate with Methyl Vinyl Ketone. Journal of Organic Chemistry. 1964 Apr 1;29(4):787–9.
Spencer, T. A., et al. “Condensation of Diethyl Malonate with Methyl Vinyl Ketone.” Journal of Organic Chemistry, vol. 29, no. 4, Apr. 1964, pp. 787–89. Scopus, doi:10.1021/jo01027a004.
Spencer TA, Newton MD, Baldwin SW. Condensation of Diethyl Malonate with Methyl Vinyl Ketone. Journal of Organic Chemistry. 1964 Apr 1;29(4):787–789.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

10.1021/jo01027a004

EISSN

1520-6904

ISSN

0022-3263

Publication Date

April 1, 1964

Volume

29

Issue

4

Start / End Page

787 / 789

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry