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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.

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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]

References

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