Tetrahydropyran

Tetrahydropyran
IUPAC name Oxane
Other names Tetrahydropyran, Oxacyclohexane
Identifiers
CAS number	142-68-7 Y
PubChem	8894
ChemSpider	8554 Y
UNII	V06I3ILG6B Y
DrugBank	DB02412
KEGG	C15345 Y
ChEBI	CHEBI:46941 Y
Jmol-3D images	Image 1
SMILES O1CCCCC1
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
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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, tetrahydropyran ring system, i.e. a 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

• Tetrahydrofuran (THF)
• Pyran

References

1. ^ D. W. Andrus; John R. Johnson (1955), "Tetrahydropyran", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0794 ; Coll. Vol. 3: 794 
2. ^ R. A. Earl L. B. Townsend (1990), "Methyl 4-Hydroxy-2-butynoate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv7p0334 ; Coll. Vol. 7: 334 
3. ^ Arthur F. Kluge (1990), "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv7p0160 ; Coll. Vol. 7: 160