Methyl chloroacetate → HCID 18969559, compound

HRID 399017

Reaction equation

HRID 399017 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CC(C)=O>[CH3:16][O:15][C:13]([CH2:12][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)=[O:14]

Participants

6

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 5245086-Hydroxyindole

Product 1

HCID 18969559HCID 18969559, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

6-Hydroxyindole (2.9 g), methyl chloroacetate (2.7 g), potassium carbonate (5.5 g) and potassium iodide (0.2 g) are added to acetone (100 ml), and the mixture is refluxed for 8 hours. The reaction mixture is cooled to room temperature, and the insoluble materials are removed by filtration. The filtrate is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform) to give 6-methoxycarbonylmethoxyindole (2.83 g).

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. customthe insoluble materials are removed by filtration
  3. customThe filtrate is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-59f19f98a90542538f9d78d9b52ab590
Source dataset
uspto-grants-1998_10
Patent number
US05817689

Linked notes

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