تفاعل #78267

معادلة التفاعل

4-hydroxyindole

2-chloroethanol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

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

المذيبات

diethyl ether

tetrahydrofuran

Et2O hexane

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated in vacuo
2. 2
   أخرىto give a residue
3. 3
   أخرىthe solid triphenylphosphine oxide is precipitated
4. 4
   أخرىremoved by filtration
5. 5
   تركيزThe filtrate is concentrated
6. 6
   أخرىpurified by flash chromatography (silica gel, EtOAc/hexane: 1.5/8.5)
7. 7
   أخرىto give an oil

الإجراء التجريبي

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.

المصدر