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Tetrahydropyran



Tetrahydropyran
IUPAC name Tetrahydropyran
Identifiers
CAS number 142-68-7
SMILES C1CCCCO1
Properties
Molecular formula C5H10O
Molar mass 86.13 g/mol
Density 0.880 g/cm3
Melting point

-45 °C, 228 K, -49 °F

Boiling point

88 °C, 361 K, 190 °F

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Tetrahydropyran, or oxane, is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom.

Additional recommended knowledge

The tetrahydropyran ring system is the core of pyranose sugars.

In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[1][2] 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.

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[3]

See also

References

  1. ^ R. A. Earl L. B. Townsend (1990). "Methyl 4-Hydroxy-2-butynoate". Org. Synth.; Coll. Vol. 7: 334. 
  2. ^ Arthur F. Kluge (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate". Org. Synth.; Coll. Vol. 7: 160. 
  3. ^ D. W. Andrus; John R. Johnson (1955). "Tetrahydropyran". Org. Synth.; Coll. Vol. 3: 794. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tetrahydropyran". A list of authors is available in Wikipedia.
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