Reaction #2069970

Reaction equation

benzenesulfonyl chloride

NaHCO3

4-(2-chloroethoxy)-1H-indole

sodium hydride

→

title compound

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

Solvents

EtOAc

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   OtherThe resultant phases are separated
3. 3
   ExtractionThe aqueous phase is extracted with EtOAc
4. 4
   Washthe combined organic phase is washed sequentially with H2O and saturated NaCl
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otherto give a residue
8. 8
   OtherThe residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/8)

Procedure

A stirred solution of 4-(2-chloroethoxy)-1H-indole (3.4 g, 17.4 mmol) in tetrahydrofuran is treated with sodium hydride (60% in mineral oil, 1.04 g, 26.1 mmol) under nitrogen at room temperature, stirred for 30 minutes, treated with benzenesulfonyl chloride (3.4 mL, 26.1 mmol) stirred at room temperature overnight and treated with saturated NaHCO3 and EtOAc. The resultant phases are separated. The aqueous phase is extracted with EtOAc and the combined organic phase is washed sequentially with H2O and saturated NaCl, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/8) to give the title compound as an off-white solid, 4.94 g (86%), mp 85-87° C., identified by NMR and mass spectral analyses.

Source