Tetrahydropyran

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Tetrahydropyran
Tetrahydropyran THP
Identifiers
CAS number 142-68-7 YesY
PubChem 8894
ChemSpider 8554 YesY
UNII V06I3ILG6B YesY
DrugBank DB02412
KEGG C15345 YesY
ChEBI CHEBI:46941 YesY
Jmol-3D images Image 1
Properties
Molecular formula C5H10O
Molar mass 86.13 g/mol
Density 0.880 g/cm3
Melting point −45 °C (−49 °F; 228 K)
Boiling point 88 °C (190 °F; 361 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose.

Preparation[edit]

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

Reactions[edit]

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.

THP protective groups

See also[edit]

References[edit]

  1. ^ D. W. Andrus; John R. Johnson (1955), "Tetrahydropyran", Org. Synth. ; Coll. Vol. 3: 794 
  2. ^ R. A. Earl L. B. Townsend (1990), "Methyl 4-Hydroxy-2-butynoate", Org. Synth. ; Coll. Vol. 7: 334 
  3. ^ Arthur F. Kluge (1990), "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate", Org. Synth. ; Coll. Vol. 7: 160