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3,4-Dihydropyran

3,4-Dihydropyran (DHP) is a heterocyclic compound with the formula C5H8O. The six-membered C5O ring has the unsaturation adjacent to oxygen. The isomeric 3,6-dihydropyran has a methylene separating the double bond and oxygen. DHP is used for protecting group for alcohols. It is a colorless liquid.

Preparation

Dihydropyran is prepared by the dehydration of tetrahydrofurfuryl alcohol over alumina at 300–400 °C. THFA is itself prepared from tetrahydro-2-furoic acid. :[[File:Pyranprep.png|270px]]

Reactions

In organic synthesis, the 2-tetrahydropyranyl (THP) group is used as a protecting group for alcohols. Reaction of the alcohol with DHP forms a THP ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored by acidic hydrolysis, concomitant with formation of 5-hydroxypentanal.

:[[File:THPmeth.png|thumb|center|320 px|Protection of an alcohol as THP ether followed by its deprotection. Both steps require acid catalysts.]]

References

References

  1. (2001). "3,4-Dihydro-2H-pyran". EEROS.
  2. R. L. Sawyer and D. W. Andrus. (1955). "2,3-Dihydropyran".
  3. R. A. Earl L. B. Townsend. (1990). "Methyl 4-Hydroxy-2-butynoate".
  4. Arthur F. Kluge. (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate".
  5. (2006). "Greene's Protective Groups in Organic Synthesis".
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