Reaktion #43311

ord-03e023041a31460a9e95a92d281c2f32

Reaktionsgleichung

O=c1cc(OCc2ccccc2)ccn1-c1ccc(O)cc1
4-Benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one
CN(C)CCO
2-(dimethylamino)ethanol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCOC(=O)N=NC(=O)OCC
diethyl azodicarboxylate
CN(C)CCOc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1
title compound
Ausbeute 66.6%
CN(C)CCOc1ccc(-n2ccc(OCc3ccccc3)cc2=O)cc1
4-benzyloxy-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1H-pyridin-2-one
Ausbeute 66.6%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenConcentrating
  2. 2
    Sonstigethe reaction liquid under reduced pressure
  3. 3
    Sonstigethe resulting residue was purified on silica gel column chromatography (C-300, methanol: chloroform=1:20-1:10)

Vorschrift

4-Benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one (150 mg, 0.511 mmol), 2-(dimethylamino)ethanol (0.057 mL, 0.562 mmol), triphenylphosphine (269 mg, 1.02 mmols) and diethyl azodicarboxylate (0.163 mL, 1.02 mmols) were stirred overnight in THF (4 mL). Concentrating the reaction liquid under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300, methanol: chloroform=1:20-1:10) to provide the title compound (124 mg, 60%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732456B2uspto-grants-2010_06