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

HRID 1887418

Reaktionsgleichung

Reaktionsgleichung von HRID 1887418
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)[CH2:2][CH:3]=[CH2:4]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 693893-Buten-1-olHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 3199452-But-3-enoxyoxaneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 1000 ml rb flask were placed 3-buten-1-ol (7.21 g, 100.00 mmol), 3,4-dihydro-2H-pyran (12.62 g, 150.00 mmol) and pyridinium p-toluenesulfonate (2.51 g, 10.00 mmol) in 350 ml of anhydrous dichloromethane. The reaction mixture was stirred at room temperature for 4 h. Then the reaction mixture was concentrated and the residue was purified by column with Hexane/Ethyl acetate=100/5 to provide 13.90 g of the desired product as an oil (89.0%). 1H-NMR (DMSO-d6) δ 5.851-5.742 (m, 1H), 5.103-5.011 (d, 1H), 4.997-4.985 (d, 1H), 4.555-4.537 (t, 1H), 3.745-3.611 (m, 2H), 3.433-3.347 (m, 2H), 2.290-2.236 (m, 2H), 1.698-1.675 (m, 2H), 1.611-1.566 (m, 4H).

Aufarbeitung

  1. customIn a 1000 ml rb flask were placed
  2. concentrationThen the reaction mixture was concentrated
  3. customthe residue was purified by column with Hexane/Ethyl acetate=100/5

Quellen und Nachweise

ORD-Eintrag
ord-b9887947d73e43e8bac1958882e96144
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501755B2

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