Triphenylphosphine → methyl 2-[4-[((3R)-tetrahydro-3-furanyl)oxy]phenyl]-2-oxoacetate

HRID 53975

Reaktionsgleichung

Reaktionsgleichung von HRID 53975
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.O[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:4]1[CH2:5][CH2:6][C@@H:2]([O:1][C:8]2[CH:9]=[CH:10][C:11]([C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[CH2:3]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Produkt 1

HCID 53727378methyl 2-[4-[((3R)-tetrahydro-3-furanyl)oxy]phenyl]-2-oxoacetateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 30 ml of tetrahydrofuran were dissolved 3.0 g of (S)-(+)-3-hydroxytetrahydrofuran, 6.6 g of methyl 2-(4-hydroxyphenyl)-2-oxoacetate and 8.90 g of triphenylphosphine. The thus prepared solution was mixed with 6.0 g of diethyl azodicarboxylate, and the mixture was stirred for 2 hours. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using chloroform as an eluant, thereby obtaining 4.60 g of methyl 2-[4-[((3R)-tetrahydro-3-furanyl)oxy]phenyl]-2-oxoacetate in an oily form.

Aufarbeitung

  1. distillationAfter distilling off the solvent
  2. customthe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-3d85a87aa96c4092ba160e7763a9d1f3
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620991

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