Water → Ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-oxo-1h-indole-3-acetate

HRID 1384833Notes

Reaction equation

HRID 1384833 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:16]2[CH3:19])=[CH:12][CH:11]=1.ClCCl.O>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:16]2[CH3:19])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 20884Ethoxalyl chlorideHCID 10561874Ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 15461899Ethyl 6-chloro-2-(ethoxycarbonyl)-1-methyl-oxo-1h-indole-3-acetateYield 84.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

4 ml (36.4 mmol) of titanium(IV) chloride are added to a solution of 4 ml (36 mmol) of ethyl chlorooxoacetate in 100 ml of 1,2-dichloroethane. The reaction mixture is stirred for 30 min at room temperature, 7.8 g (32.8 mmol) of ethyl 6-chloro-1-methyl-1H-indole-2-carboxylate are then added and the reaction mixture is stirred for 4 hours at room temperature. The mixture is cooled and 200 ml of dichloromethane and 100 ml of water are added. The organic phase is separated by settling, washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure and the residue is purified by chromatography on a column of silica gel. 9.4 g (27.7 mmol) of product are isolated.

Workup

  1. stirringthe reaction mixture is stirred for 4 hours at room temperature
  2. temperatureThe mixture is cooled
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue is purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-b3752bbd4b624d64b297ff7f8f5e3c2d
Source dataset
uspto-grants-2001_07
Patent number
US06262045B1

Reaction notes

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