Reacción #78267

Ecuación de reacción

4-hydroxyindole

2-chloroethanol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

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

Disolventes

diethyl ether

tetrahydrofuran

Et2O hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   Otroto give a residue
3. 3
   Otrothe solid triphenylphosphine oxide is precipitated
4. 4
   Otroremoved by filtration
5. 5
   ConcentraciónThe filtrate is concentrated
6. 6
   Otropurified by flash chromatography (silica gel, EtOAc/hexane: 1.5/8.5)
7. 7
   Otroto give an oil

Procedimiento

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.

Fuente