Tetrahydropyran
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| Template:Chembox header| 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 |
| Template:Chembox header | 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.
One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[3]
See also
- Tetrahydrofuran (THF)
- Pyran
References
- ^ Organic Syntheses, Coll. Vol. 7, p.334 (1990); Vol. 60, p.81 (1981) Article.
- ^ Organic Syntheses, Coll. Vol. 7, p.160 (1990); Vol. 64, p.80 (1986) Article.
- ^ Organic Syntheses, Coll. Vol. 3, p.794 (1955); Vol. 23, p.90 (1943).Article