Tetrahydropyran

Tetrahydropyran
Tetrahydropyran THP
Chemical name	Tetrahydropyran
Chemical formula	C5H10O
Molecular mass	86.13 g/mol
CAS number	[142-68-7]
Density	0.880 g/cm3
Melting point	-45 °C
Boiling point	88 °C
SMILES	C1CCCCO1
Disclaimer and references

Overview

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 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.

THP protective groups

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.^[3]

See also

• Tetrahydrofuran (THF)
• Pyran

References

1. ^  Organic Syntheses, Coll. Vol. 7, p.334 (1990); Vol. 60, p.81 (1981) Article.
2. ^  Organic Syntheses, Coll. Vol. 7, p.160 (1990); Vol. 64, p.80 (1986) Article.
3. ^  Organic Syntheses, Coll. Vol. 3, p.794 (1955); Vol. 23, p.90 (1943).Article

External links

nl:Tetrahydropyraan