Potassium Carbonate → HCID 22627470, compound

HRID 278085Notes

Reaction equation

HRID 278085 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[CH:6]=[C:5]1[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:23][O:22][C:20]([CH2:19][CH2:18][CH2:17][C:5]1[NH:4][C:12]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)=[O:21]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22627351HCID 22627351, compound

Product 1

HCID 22627470HCID 22627470, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-acetyl-2-(3-methoxycarbonylpropyl)indole-6-carboxylate (2.34 g) in methanol (20 ml) was added powdered potassium carbonate (1.04 g), and the mixture was stirred under reflux for 10 minutes. The resulting mixture was evaporated in vacuo and the residue was acidified with 1N hydrochloric acid and extracted with chloroform. The organic phase was washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate and then evaporated in vacuo. The residue was triturated with ether to give methyl 2-(3-methoxycarbonylpropyl)indole-6-carboxylate (1.23 g) as solid.

Workup

  1. temperatureunder reflux for 10 minutes
  2. customThe resulting mixture was evaporated in vacuo
  3. extractionextracted with chloroform
  4. washThe organic phase was washed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-02b19a949f2f41279b100ffea181f0b2
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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