Reaktion #1006235

ord-1c0a5ec6736c4bba97a1ba8ffb48b2a3

Reaktionsgleichung

O=Cc1cccnc1Br
2-Bromo-pyridine-3-carbaldehyde
[Br][Mg][CH2]CCc1ccccc1
3-phenyl-propyl magnesium bromide
OC(CCCc1ccccc1)c1cccnc1Br
title compound
OC(CCCc1ccccc1)c1cccnc1Br
1-(2-Bromo-pyridin-3-yl)-4-phenyl-butan-1-ol

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITat room temperature for 30 minutes
  2. 2
    Sonstigecomplete was quenched with 10 mL of NH4Cl (sat'd, aq.)
  3. 3
    SonstigeThe crude material was purified on silica gel (0-100% EtOAc in hexanes)

Vorschrift

2-Bromo-pyridine-3-carbaldehyde (1.25 g, 6.72 mmol) was dissolved in THF (10 mL) and cooled to 0° C. 3-phenyl-propyl magnesium bromide (0.5 M in THF, 20.2 mL, 10.08 mmol) was slowly added and the reaction stirred at 0° C. for 1 hour and then at room temperature for 30 minutes. The reaction was monitored by TLC and when complete was quenched with 10 mL of NH4Cl (sat'd, aq.). The volume of THF was reduced and the reaction was submitted to EtOAc/H2O workup. The crude material was purified on silica gel (0-100% EtOAc in hexanes) to give the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09272990B2uspto-grants-2016_03