Water → Methyl [(1H-indol-5-yl)oxy]acetate

HRID 2355257Notes

Reaction equation

HRID 2355257 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][CH2:22]C)=[O:20].O>CC(C)=O.C(Cl)Cl>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 160545-Hydroxyindole

Product 1

HCID 59808925Methyl [(1H-indol-5-yl)oxy]acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-hydroxyindole (5.00 g; 37.6 mmol), caesium carbonate (26.9 g, 82.6 mmol) and ethyl bromoacetate (4.60 g, 30.0 mmol) in 100 ml acetone is stirred for 18 hours at ambient temperature. Then the reaction mixture is combined with water and DCM. The phases are separated and the aqueous phase is extracted with DCM. The combined phases are dried on sodium sulphate and freed from the solvent in vacuo.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with DCM
  3. customThe combined phases are dried on sodium sulphate

Sources & evidence

ORD record
ord-fcd5193f926f4eea8bbee093f190ba5e
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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