3,4-dihydro-2H-pyran → 2-(4-Pentynyloxy)tetrahydro-2H-pyran

HRID 715961

Reaktionsgleichung

Reaktionsgleichung von HRID 715961
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[CH2:8][CH2:9][C:10]#[CH:11].C(=O)(O)[O-].[Na+]>CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:7]([O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:8][CH2:9][C:10]#[CH:11]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 793464-Pentyn-1-olHCID 516892Sodium Bicarbonate

Produkt 1

HCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyranAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6101p-Toluenesulfonic acidKatalysator

Versuchsvorschrift

3,4-Dihydro-2H-pyran (5.0 g) was added dropwise to an ice cooled mixture of 4-pentyn-1-ol (5.0 g) and 4-methylbenzenesulfonic acid (0.512 g). The resultant mixture was stirred at room temperature for 4 hours. Solid sodium bicarbonate (1.0 g) was added and the mixture was stirred for 10 minutes, then filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give 2-(pent-4-ynyloxy)tetrahydropyran (7.72 g) as a clear oil.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Quellen und Nachweise

ORD-Eintrag
ord-3562ee54fdb14a73bf66059033640eed
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187494B2

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