2-Butene-1,4-diol → (Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol

HRID 36579

Reaktionsgleichung

Reaktionsgleichung von HRID 36579
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[CH:8]=[CH:9][CH2:10][OH:11].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.O1CCCC1>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH2:10]/[CH:9]=[CH:8]\[CH2:7][OH:12]

Komponenten

5

Edukt 3

HCID 80652-Butene-1,4-diolHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 10975949(Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-olAusbeute 481,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21919333Tetrahydrofurane dichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dihydropyran (9.1 ml, 100 mmol) was added dropwise to a cooled (0° C.) solution of 2-butene-1,4-diol (8.8 g, 10 mmol) and pyridinium paratoluenesulfonate (0.25 g, 10 mmol) in anhydrous dichloromethane:tetrahydrofuran (2:1). The mixture was stirred two days at 0° C. then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexane 3:7) to give 8.3 g of the title compound (49%).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (ethyl acetate:hexane 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-0deb034b167b441282245b88540d7147
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416076

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