3,4-dihydro-2H-pyran → 2-But-3-enoxyoxane

HRID 1582515

Reaktionsgleichung

Reaktionsgleichung von HRID 1582515
P(Cl)(Cl)(Cl)=O.[CH2:6]([OH:10])[C:7]#[C:8][CH3:9].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl>[CH2:6]([O:10][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[CH2:7][CH:8]=[CH2:9]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 129912-Butyn-1-olHCID 24813Phosphorus oxychloride

Produkt 1

HCID 3199452-But-3-enoxyoxane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of phosphoryl chloride (0.5 ml in 10 ml of DCM) was added with care to a solution of but-2-yn-1-ol (8.75 g, 125 mmol) and dihydropyran (10.50 g, 125 mmol) in DCM (80 ml). The reaction mixture was stirred at room temperature for 16 h, washed with sodium hydrogen carbonate solution (3 times), dried (MgSO4) and the solvent removed in vacuo to yield a colorless oil. The crude product was purified by column chromatography [silica gel, euted with hexane/ethyl acetate (4:1), Rf: 0.36] to yield a colorless oil.

Aufarbeitung

  1. washwashed with sodium hydrogen carbonate solution (3 times)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customto yield a colorless oil
  5. customThe crude product was purified by column chromatography [silica gel, euted with hexane/ethyl acetate (4:1), Rf: 0.36]
  6. customto yield a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-1813885332774ff78541c40e688d6bc8
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737124B2

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