Tetrahydropyran

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Tetrahydropyran
IUPAC name

Oxane

Other names

Tetrahydropyran,
Oxacyclohexane

Identifiers
CAS number 142-68-7 YesY
PubChem 8894
ChemSpider 8554 YesY
UNII V06I3ILG6B YesY
DrugBank DB02412
KEGG C15345 YesY
ChEBI CHEBI:46941 YesY
Jmol-3D images Image 1
Properties
Molecular formula 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
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tetrahydropyran 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, tetrahydropyran ring system, i.e. a five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose.

Preparation

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[1]

Reactions

In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[2][3] 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.

See also

References

  1. ↑ D. W. Andrus; John R. Johnson (1955), "Tetrahydropyran", Org. Synth. ; Coll. Vol. 3: 794 
  2. ↑ R. A. Earl L. B. Townsend (1990), "Methyl 4-Hydroxy-2-butynoate", Org. Synth. ; Coll. Vol. 7: 334 
  3. ↑ Arthur F. Kluge (1990), "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate", Org. Synth. ; Coll. Vol. 7: 160 
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