Английская Википедия:3,4-Dihydropyran

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Версия от 22:18, 25 декабря 2023; EducationBot (обсуждение | вклад) (Новая страница: «{{Английская Википедия/Панель перехода}} {{chembox | Watchedfields = changed | verifiedrevid = 369887408 | Name = Dihydropyran | ImageFile1 = Structural formula of 3,4-dihydro-2H-pyran.svg | ImageSize1 = 90px | ImageName1 = 3,4-dihydropyran skelet | ImageCaptionL2 = 3,4-dihydropyran | PIN=3,4-Dihydro-2''H''-pyran | OtherNames= 2,3-Dihydro-4''H''-pyran, DHP |Section1={{Chembox Identifiers | InChI = 1/C5H8O/c1-2-4-6-5-3-1/h2,4H...»)
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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.[1]

Preparation

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

Файл:Pyranprep.png

Reactions

In organic synthesis, the 2-tetrahydropyranyl (THP) group is used as a protecting group for alcohols.[3][4] 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.[5]

Файл:THPmeth.png
Protection of an alcohol as THP ether followed by its deprotection. Both steps require acid catalysts.

See also

References

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