Reaktion #78267

Reaktionsgleichung

4-hydroxyindole

2-chloroethanol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

4-(2-Chloroethoxy)-1H-Indole

Lösungsmittel

diethyl ether

tetrahydrofuran

Et2O hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated in vacuo
2. 2
   Sonstigeto give a residue
3. 3
   Sonstigethe solid triphenylphosphine oxide is precipitated
4. 4
   Sonstigeremoved by filtration
5. 5
   EinengenThe filtrate is concentrated
6. 6
   Sonstigepurified by flash chromatography (silica gel, EtOAc/hexane: 1.5/8.5)
7. 7
   Sonstigeto give an oil

Vorschrift

A solution of 4-hydroxyindole (3.99 g, 30 mmol), 2-chloroethanol (6.03 ml, 90 mmol) and triphenylphosphine (23.6 g, 90 mmol) in tetrahydrofuran is treated with diethyl azodicarboxylate (14.1 ml, 90 mmol) under nitrogen at room temperature, stirred for 2 hr at room temperature and concentrated in vacuo to give a residue. Cooled diethyl ether is added to the residue and the solid triphenylphosphine oxide is precipitated and removed by filtration. The filtrate is concentrated and purified by flash chromatography (silica gel, EtOAc/hexane: 1.5/8.5) to give an oil. After trituration with Et2O/hexane (1/10), the title compound is obtained as a white solid, 4.8 g (82%) mp 60° C., identified by NMR and mass spectral analyses.

Quelle