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Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate

  • CAS No. 103260-44-2

  • Cat. No. CS-D1493
  • Purity≥97%
  • MDL No.MFCD03788560

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

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate|CS-D1493

Structure of 103260-44-2

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General Information

  • CAS No. 103260-44-2
  • Cat. No. CS-D1493
  • Purity ≥97%
  • MDL No. MFCD03788560
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₆O₃
  • Molecular Weight 172.22
  • Synonym(s) (Tetrahydropyran-4-yl)acetic acid ethyl ester; Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate; Ethyl tetrahydropyran-4-acetate; ETHYL TETRAHYDROPYRAN-4-YL-ACETATE
  • SMILES O=C(OCC)CC1CCOCC1

Description

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate serves as a robust, bench-stable building block for complex synthesis. The tetrahydropyranyl group provides exceptional stability and selective protection of alcohols, while the ester functionality enables facile transformation. This compound integrates seamlessly into multi-step sequences requiring orthogonal reactivity and reliable handling under standard conditions.

Application

Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate serves as a versatile building block in synthetic organic chemistry, enabling the efficient construction of complex heterocyclic scaffolds and bioactive molecules. The tetrahydropyranyl group provides robust protection for diols and hydroxyl functionalities under acidic conditions, while the ester and α-methylene functionality facilitate subsequent transformations such as nucleophilic additions, reductions, and cross-coupling reactions. Its bench stability and ease of purification make it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • American Cyanamid Company Patent: US6340691 B1, 2002 ; Location in patent: Page column 66 ; US 6340691 B1
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 71, # 26 p. 9909 - 9911

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   35.53
  • LogP   1.3662
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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