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609-09-6 - Diethyl ketomalonate, 95% - Diethyl mesoxalate - Diethyl oxomalonate - A12771 - Alfa Aesar

A12771 Diethyl ketomalonate, 95%

CAS Number
609-09-6
Synonyms
Diethyl mesoxalate
Diethyl oxomalonate

Size Price ($) Quantity Availability
5g 35.36
25g 145.80
100g 507.60
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Diethyl ketomalonate, 95%

MDL
MFCD00009121
EINECS
210-176-2

Chemical Properties

Formula
C7H10O5
Formula Weight
174.15
Melting point
ca -70°
Boiling Point
208-210°
Flash Point
>110°(230°F)
Density
1.142
Refractive Index
1.4150
Sensitivity
Moisture Sensitive
Solubility
Fully miscible with water.

Applications

Diethyl ketomalonate, reagent employed in Wittig and Aza-Wittig reactions for synthesis of triazoles, and 2-azadienes, respectively.

Notes

Moisture Sensitive. Store in cool dry place in tightly closed container. With good ventilation. Store away from oxidizing agent and water/moisture.

Literature References

D. Basavaiah; V. V. L. Gownswari. Diethyl Ketomalonate: A Fast Reacting Substrate for Baylis-Hillman Reaction. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 1989,(13-14), 6898-6904.

M. Sugawara; M.M. Baizer. Electrogenerated bases VII. Novel syntheses of ethyl glyoxalate and diethyl ketomalonate via electrogenerated superoxide. Tetrahedron Letters. 1983,24(22), 2223-2226.

The carbonyl group behaves as a heterodienophile towards simple dienes. Curtius degradation of the gem-diester to carbonyl completes a synthesis of ß-unsaturated δ-lactones: Rocz. Chem., 38, 707 (1964); J. Am. Chem. Soc., 97, 6892 (1975); J. Org. Chem., 42, 4095 (1977):

For asymmetric Diels-Alder reaction, see: J. Chem. Soc., Chem. Commun., 676 (1987). For addition to aza-dienes, see: Tetrahedron Lett, 30, 2685 (1989).

Ene-addition to alkenes occurs at the less-substituted carbon. Oxidative degradation leads to ß-unsaturated carboxylic acids: J. Am. Chem. Soc., 102, 2473 (1980); 106, 3797 (1984):

Thus, the reagent could be regarded as a CO2 equivalent in both the above sequences.

Undergoes the Baylis-Hillman reaction in which a carbanionic species, generated by the reversible addition of 1,4-Diazabicyclo[2.2.2]octane, A14003, to a Michael acceptor, adds to the carbonyl group: Synth. Commun., 19, 2461 (1989).

Reacts with activated arenes under Friedel-Crafts conditions, or with aryllithium or Grignard derivatives, to give aryl hydroxymalonates, hydrolysis and decarboxylation of which gives substituted mandelic acids: Org. Synth. Coll., 3, 326 (1955). Alternatively, they may be transformed reductively to arylmalonates and hence to ester enolates: J. Org. Chem., 47, 4692 (1982).

Other References

Merck
14,5913
Beilstein
971873
Harmonized Tariff Code
2918.30
TSCA
Yes

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