Reaction #2069972

Reaction equation

2-{[1-(phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

triphenylphosphine

→

title compound

2-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylamine

Solvents

tetrahydrofuran

water

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   ConcentrationThe filtrate is concentrated in vacuo
3. 3
   Otherthe resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 8.5/1.5/0.05)

Procedure

A mixture of 2-{[1-(phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide (3.3 g, 9.6 mmol) and triphenylphosphine (3.67 g, 14 mmol) in tetrahydrofuran and water is stirred under nitrogen for 24 hr at room temperature and filtered. The filtrate is concentrated in vacuo and the resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 8.5/1.5/0.05) to afford the title compound as an off-white solid, 2.54 g (80%), mp 71-73° C., identified by NMR and mass spectral analyses.

Source