Triphenylphosphine → HCID 140398709, Verbindung

HRID 1419727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419727
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:13]/[OH:14])/[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8].[CH:15]([O:28][C:29]1[C:30](=[O:37])[CH:31]=[C:32]([CH2:35]O)[O:33][CH:34]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:13]/[O:14][CH2:35][C:32]1[O:33][CH:34]=[C:29]([O:28][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:30](=[O:37])[CH:31]=1)/[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 143063875-(benzhydryloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 15093893HCID 15093893, Verbindung

Produkt 1

HCID 140398709HCID 140398709, VerbindungAusbeute 207,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice cooled solution of allyl (E)-2-(2-thienyl)-2-(hydroxyimino)acetate (1.0 gm, 4.734 mmol), 5-benzhydryloxy-2-(hydroxymethyl) pyran-4-one (1.46 gm, 4.734 mmol) and triphenylphosphine (1.24 gm, 4.734 mmol) in dry THF (30 ml) under nitrogen was added dropwise diethyl azodicarboxylate (820 μl, 5.208 mmol). The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure to afford the crude as yellow gum (4.93 gm). The product was purified by silica gel column chromatography using hexane-ethyl acetate (2:1) as eluant to provide the title compound as a gummy foam in 47% yield (1.11 gm).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7591388962854cca93938c3e132549b9
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05888998

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