Reaktion #1435743

Reaktionsgleichung

water

(3-pyridyl)diethylborane

2-(4-bromophenyl)ethanol

KOH

→

title product

3-[4-(2-Hydroxyethyl)phenyl]pyridine

Lösungsmittel

ethyl acetate

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Temperaturat reflux under a stream of argon for 4 hours
3. 3
   Sonstigethe organic phase is dried
4. 4
   Sonstigethe solvent is evaporated
5. 5
   SonstigeThe residue is purified by chromatography on a column of silica gel, elution

Vorschrift

1 g (6.8 mmol) of (3-pyridyl)diethylborane, 0.87 ml (10.2 mmol) of 2-(4-bromophenyl)ethanol, 1.53 g (27 mmol) of KOH powder, 1.1 g (3.4 mmol) of tetrabutylammonium bromide and 0.39 g (0.34 mmol) of tetrakis(triphenylphosphine)Pd are mixed in 25 ml of anhydrous THF. The mixture is heated at reflux under a stream of argon for 4 hours. The mixture is poured into water, extraction is carried out with ethyl acetate, the organic phase is dried and the solvent is evaporated. The residue is purified by chromatography on a column of silica gel, elution being carried out with a cyclohexane/ethyl acetate=1/1 mixture, the title product thus being obtained.

Quelle