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Triphenylphosphine → 3-(3-Quinuclidinyloxy)isoxazole

HRID 263454
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 263454
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1.O[CH:39]1[CH:44]2[CH2:45][CH2:46][N:41]([CH2:42][CH2:43]2)[CH2:40]1>O1CCCC1>[N:41]12[CH2:46][CH2:45][CH:44]([CH2:43][CH2:42]1)[CH:39]([O:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1)[CH2:40]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 15381(+-)-3-QuinuclidinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516613HCID 178516613, Verbindung

Produkt 1

HCID 101980493-(3-Quinuclidinyloxy)isoxazoleAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of 9.18 g of triphenylphosphine in 100 ml of tetrahydrofuran was cooled to 5° C. 6.10 g of diethyl azodicarboxylate were then added dropwise to the cooled solution, after which 2.98 g of 3-hydroxyisoxazole and 4.45 g of 3-hydroxyquinuclidine were added, and the resulting mixture was stirred at room temperature for 24 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to afford 5.18 g (yield 76.2%) of the title compound as a colorless powder, melting at 80°-81° C.

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-45a5c665ce2f43eeabe63b686c57eea9
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05643923

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