Diethyl ketomalonate

• Catalog No.: A12771
• CAS Number: 609-09-6
• M. F.: C7H10O5
• M. W.: 174.1513
• Purity: 95%

SYNONYMS

• Title: 酮基丙二酸二乙酯
• IUPAC name: 1,3-diethyl 2-oxopropanedioate
• IUPAC Traditional name: 1,3-diethyl 2-oxopropanedioate
• Synonyms: Diethyl oxomalonate; Diethyl mesoxalate

DATABASE IDS

• Merck Index: 145913
• MDL Number: MFCD00009121
• Beilstein Number: 971873
• CAS Number: 609-09-6
• EC Number: 210-176-2

PROPERTIES

• Purity: 95%
• Boiling Point: 208-210°C
• Density: 0.927
• Flash Point: >110°C(230°F)
• Melting Point: ca -70°C
• Refractive Index: 1.4175
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是

REFERENCES

• The carbonyl group behaves as a heterodienophile towards simple dienes. Curtius degradation of the gem-diester to carbonyl completes a synthesis of ?-unsaturated δ-lactones: Rocz. Chem., 38, 707 (1964); J. Am. Chem. Soc., 97, 6892 (1975); J. Org. Chem., 42, 4095 (1977):
  
• Ene-addition to alkenes occurs at the less-substituted carbon. Oxidative degradation leads to ?-unsaturated carboxylic acids: J. Am. Chem. Soc., 102, 2473 (1980); 106, 3797 (1984):
  
• For asymmetric Diels-Alder reaction, see: J. Chem. Soc., Chem. Commun., 676 (1987). For addition to aza-dienes, see: Tetrahedron Lett, 30, 2685 (1989).
• 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).