No.102
Malonic Acid Derivative
| A1487 | Acetonylmalonic Acid Dimethyl Ester (1) |
5g 1g |
The present reagent 1 is a malonic acid derivative containing a carbonyl group and employed in the synthesis of a cyclic compound as a bifunctional building block. C. Mercier, et al . have reported the usefulness of 1 in the synthesis of a cyclic enone 2 via condensation between the cyclic ketal of 1 and α-chlorocyclopentanone in the presence of a base, followed by hydrolysis and ring-closing reaction. E. E. Schweizer, et al . also have reported usefulness of 1 by synthesis of cyclopentene 3 from the reaction of 1 with a vinyl phosphonium salt.
References
1) Reaction with α-chloro carbonyl compound
C. Mercier, A. R. Addas, P. Deslongchamps, Can. J. Chem., 50, 1882 (1972)
2) Reactions with phosphonium salts
E. E. Schweizer, G. J. O'Neill, J. Org. Chem., 30, 2082 (1965)
A. G. Cameron, A. T. Hewson, J. Chem. Soc., Perkin Trans. 1, 1983, 2979
Y. Okada, T. Minami, S. Yahiro, K. Akinaga, J. Org. Chem., 54, 974 (1989)
C. Mercier, A. R. Addas, P. Deslongchamps, Can. J. Chem., 50, 1882 (1972)
2) Reactions with phosphonium salts
E. E. Schweizer, G. J. O'Neill, J. Org. Chem., 30, 2082 (1965)
A. G. Cameron, A. T. Hewson, J. Chem. Soc., Perkin Trans. 1, 1983, 2979
Y. Okada, T. Minami, S. Yahiro, K. Akinaga, J. Org. Chem., 54, 974 (1989)
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