Tetrahydropyran

Tetrahydropyran

Tetrahydropyran THP
Names
IUPAC name Oxane
Other names Tetrahydropyran, Oxacyclohexane
Identifiers
CAS Number	142-68-7 Y
ChEBI	CHEBI:46941 Y
ChemSpider	8554 Y
DrugBank	DB02412 Y
Jmol 3D model	Interactive image
KEGG	C15345 Y
PubChem	8894
UNII	V06I3ILG6B Y
InChI InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2 Y Key: DHXVGJBLRPWPCS-UHFFFAOYSA-N Y InChI=1/C5H10O/c1-2-4-6-5-3-1/h1-5H2 Key: DHXVGJBLRPWPCS-UHFFFAOYAV
SMILES O1CCCCC1
Properties
Chemical 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)
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.

Preparation

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

Reactions

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

• Tetrahydrofuran (THF)
• Pyran