Tetrahydropyran
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216108429
2008-05-31T02:56:20Z
Cacycle
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+ [[Category:Ethers]]
{{Chembox new
| Name = Tetrahydropyran
| ImageFileL1 = Tetrahydropyran.png
| ImageSizeL1 = 80px
| ImageNameL1 = Tetrahydropyran
| ImageFileR1 = Oxane-3D-vdW.png
| ImageSizeR1 = 100px
| ImageNameR1 = THP
| IUPACName = Tetrahydropyran
| Section1 = {{Chembox Identifiers
| CASNo = 142-68-7
| SMILES = C1CCCCO1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>5</sub>H<sub>10</sub>O
| MolarMass = 86.13 g/mol
| Density = 0.880 g/cm<sup>3</sup>
| MeltingPtC = -45
| BoilingPtC = 88
}}
}}
'''Tetrahydropyran''', or '''oxane''', is the [[organic compound]] consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom.
The tetrahydropyran ring system is the core of [[pyranose]] sugars.
In [[organic synthesis]], the 2-tetrahydropyranyl group is used as a [[protecting group]] for [[alcohol]]s.<ref>{{OrgSynth | title = Methyl 4-Hydroxy-2-butynoate | author = R. A. Earl L. B. Townsend | collvol = 7 | collvolpages = 334 | year = 1990 | prep = cv7p0334}}</ref><ref>{{OrgSynth | title =<nowiki>Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate</nowiki> | author = Arthur F. Kluge | collvol = 7 | collvolpages = 160 | year = 1990 | prep = cv7p0160}}</ref> 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.
:[[Image:THP ether.png|500px|THP protective groups]]
One classic procedure for the [[organic synthesis]] of tetrahydropyran is by [[hydrogenation]] with [[Raney nickel]] of dihydropyran.<ref>{{OrgSynth | title = Tetrahydropyran | author = D. W. Andrus; John R. Johnson | collvol = 3 | collvolpages = 794 | year = 1955 | cv3p0794}}</ref>
==See also==
* [[Tetrahydrofuran]] (THF)
* [[Pyran]]
==References==
<references/>
[[Category:Ethers]]
[[Category:Oxygen heterocycles]]
[[Category:Protecting groups]]
[[Category:Ether solvents]]
[[de:Tetrahydropyran]]
[[nl:Tetrahydropyraan]]
[[ja:テトラヒドロピラン]]