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Ethyl 2-oxotetrahydrofuran-3-carboxylate

  • CAS No. 77513-58-7

  • Cat. No. CS-0043923
  • Molecule weight158.15
  • Purity≥98%
  • MDL No.MFCD01725680

*For research and further manufacturing use only, not for direct human use.

Ethyl 2-oxotetrahydrofuran-3-carboxylate|CS-0043923

Structure of 77513-58-7

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General Information

  • CAS No. 77513-58-7
  • Cat. No. CS-0043923
  • Purity ≥98%
  • MDL No. MFCD01725680
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₄
  • Molecular Weight 158.15
  • Synonym(s) ethyl tetrahydro-2-oxofuran-3-carboxylate
  • SMILES O=C(C1C(OCC1)=O)OCC

Description

Ethyl 2-oxotetrahydrofuran-3-carboxylate serves as a versatile synthon in heterocyclic synthesis, featuring a γ-keto ester motif flanked by a saturated tetrahydrofuran ring. This structure enables direct functionalization at the C3 position and facilitates cyclization cascades under mild conditions. The molecule exhibits excellent stability under standard bench protocols and integrates readily into multistep sequences for complex oxygenated heterocycles.

Application

Ethyl 2-oxotetrahydrofuran-3-carboxylate serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to tetrahydrofuran-based scaffolds. Its α,β-unsaturated carbonyl motif facilitates Michael additions and aldol-type condensations, while the ester group supports subsequent functionalization. Bench-stable and amenable to purification by standard chromatography, it functions reliably in multistep sequences requiring orthogonal reactivity.

Synthesis

  • Route1
    • null|null
      96-48-0
    • null|null
      105-58-8
    • ~83%
    • In-stock
      Ethyl 2-oxotetrahydrofuran-3-carboxylate|CS-0043923
      77513-58-7

    References

    • Bukowska, Maria; Prejzner, Jan Polish Journal of Chemistry, 1986 , vol. 60, # 7-12 p. 957 - 959
  • Route2
    • null|null
      96-48-0
    • In-stock
      Ethyl carbonocyanidate|CS-0022374
      623-49-4
    • ~46%
    • In-stock
      Ethyl 2-oxotetrahydrofuran-3-carboxylate|CS-0043923
      77513-58-7

    References

    • Szostak, Michal; Spain, Malcolm; Choquette, Kimberly A.; Flowers, Robert A.; Procter, David J. Journal of the American Chemical Society, 2013 , vol. 135, # 42 p. 15702 - 15705
  • Route3

    References

    • Morizawa, Yoshitomi; Hiyama, Tamejiro; Oshima, Koichiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 4 p. 1123 - 1127

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   0.1126
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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