Tetrahydropyran

Tetrahydropyran
Names
IUPAC name
Oxane
Other names
Tetrahydropyran,
Oxacyclohexane
Identifiers
142-68-7 Yes
ChEBI CHEBI:46941 Yes
ChemSpider 8554 Yes
DrugBank DB02412 Yes
Jmol-3D images Image
KEGG C15345 Yes
PubChem 8894
UNII V06I3ILG6B Yes
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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, a tetrahydropyran ring system, i.e., 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, p. 794
  2. ↑ R. A. Earl L. B. Townsend (1990). "Methyl 4-Hydroxy-2-butynoate". Org. Synth.; Coll. Vol. 7, p. 334
  3. ↑ Arthur F. Kluge (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate". Org. Synth.; Coll. Vol. 7, p. 160