Reaktion #91113

ord-0bfeea6e0cdb4990ba64bd84abec8bee

Reaktionsgleichung

O=Cc1cc(F)c(OCc2ccccc2)c(F)c1
4-Benzyloxy-3,5-difluoro-benzaldehyde
O=Cc1cc(F)c(OCc2ccccc2)c(F)c1
4-benzyloxy-3,5-difluoro-benzaldehyde
CCOC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
carbethoxymethylene triphenylphosphorane
CCOC(=O)/C=C/c1cc(F)c(OCc2ccccc2)c(F)c1
title compound
Ausbeute 78.1%
CCOC(=O)/C=C/c1cc(F)c(OCc2ccccc2)c(F)c1
(E)-3-(4-benzyloxy-3,5-difluoro-phenyl)-acrylic acid ethyl ester
Ausbeute 78.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter the termination of the reaction
  2. 2
    Temperaturthe reactant was cooled
  3. 3
    Einengenconcentrated under reduced pressure
  4. 4
    SonstigeThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/10)

Vorschrift

4-Benzyloxy-3,5-difluoro-benzaldehyde (1.2 g, 4.83 mmol) obtained in Step B and carbethoxymethylene triphenylphosphorane (2.0 g, 5.78 mmol) was dissolved in THF (10 mL), and the solution was stirred at 65˜75° C. for 1 hour. After the termination of the reaction, the reactant was cooled and concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/10) to obtain the title compound (1.2 g, 78%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447044B2uspto-grants-2016_09