Tetrahydropyran

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Tetrahydropyran
Tetrahydropyran
THP
Names
IUPAC name
Oxane
Other names
Tetrahydropyran,
Oxacyclohexane
Identifiers
142-68-7 YesY
ChEBI CHEBI:46941 YesY
ChemSpider 8554 YesY
DrugBank DB02412 YesY
Jmol interactive 3D Image
KEGG C15345 YesY
PubChem 8894
UNII V06I3ILG6B YesY
Properties
C5H10O
Molar mass 86.13 g/mol
Density 0.880 g/cm3
Melting point −45 °C (−49 °F; 228 K)
Boiling point 88 °C (190 °F; 361 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. The compound is a colourless volatile liquid, but is obscure. Derivatives of tetrahydropyran are, however, more common. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. Furthermore, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose. In gas phase, the THP exists in its lowest energy Cs symmetry chair conformation.[1]

Preparation[edit]

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[2]

Reactions[edit]

In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[3][4] Reaction of the alcohol with dihydropyran forms a tetrahydropyranyl ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored readily by acidic hydrolysis with formation of 5-hydroxypentanal.

THP protective groups

See also[edit]

References[edit]

  1. ^ Builth-Williams, J. D.; Bellm, S. M.; Chiari, L.; Thorn, P. A.; Jones, D. B.; Chaluvadi, H.; Madison, D. H.; Ning, C. G.; Lohmann, B. (2013-07-21). "A dynamical (e,2e) investigation of the structurally related cyclic ethers tetrahydrofuran, tetrahydropyran, and 1,4-dioxane". The Journal of Chemical Physics 139 (3): 034306. doi:10.1063/1.4813237. ISSN 0021-9606. 
  2. ^ D. W. Andrus; John R. Johnson (1955). "Tetrahydropyran". Org. Synth. ; Coll. Vol. 3, p. 794 
  3. ^ R. A. Earl L. B. Townsend (1990). "Methyl 4-Hydroxy-2-butynoate". Org. Synth. ; Coll. Vol. 7, p. 334 
  4. ^ Arthur F. Kluge (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate". Org. Synth. ; Coll. Vol. 7, p. 160