(Triphenylphosphoranylidene)acetaldehyde → (E)-3-(5-methoxy-2-indolyl)-2-propenaldehyde

HRID 1602108

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=O)=[CH:6]2.[CH:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](/[CH:12]=[CH:16]/[CH:14]=[O:15])=[CH:6]2

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

5-Methoxyindole-2-carboxaldehyde (1.5 g, 8.5 mmol) was dissolved in dry toluene (30 ml) and treated with (formylmethylene)triphenylphosphorane (3 g, 9.8 mmol). The reaction mixture was stirred at 85° C. for 5 h, allowed to cool and chromatographed over silica gel using hexane/EtOAc (7:3). Evaporation of the solvent yielded 0.45 g (26 %) of (E)-3-(5-methoxy-2-indolyl)-2-propenaldehyde, m.p.=145-147° C.

Aufarbeitung

temperatureto cool
customchromatographed over silica gel
customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag: ord-73d513385919411a8ac8170bcc619bbe
Quelldatensatz: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05981525

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