Potassium Carbonate → ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

HRID 1096971Notes

Reaction equation

HRID 1096971 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[CH:25]1[CH2:27][CH2:26]1)(=O)C>C(O)C>[CH:25]1([N:15]2[C:16]3[C:12](=[C:11]([OH:10])[CH:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=3)[CH:13]=[CH:14]2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57930960ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate

Product 1

HCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 2.0-liter egg plant-type flask, potassium carbonate (69.58 g, 0.50 mol) was added to an ethanol (360 mL) solution of ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate (72.33 g, 0.25 mol), and stirred at room temperature for 4 hours. Ethanol was removed from the reaction solution under reduced pressure, the residue was diluted with ethyl acetate, washed with water and saturated saline water, dried with sodium sulfate, and concentrated to obtain a crude product. This was crystallized with toluene and hexane to obtain the title compound as a pale brown crystal.

Workup

  1. customEthanol was removed from the reaction solution under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water and saturated saline water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product
  7. customThis was crystallized with toluene and hexane

Sources & evidence

ORD record
ord-b02916374546452dac8cfc02dc392ea7
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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