Tetrahydropyran
IUPAC name	Tetrahydropyran
Identifiers
CAS number	142-68-7 Y
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
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Contents 1 Preparation 2 Reactions 3 See also 4 References

[edit] Preparation

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.^[1]

[edit] 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.

[edit] See also

• Tetrahydrofuran (THF)
• Pyran

[edit] 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