Ethanol → 4-Isobutoxy-1H-indole-2-carboxylic acid

HRID 2267739Notes

Reaction equation

HRID 2267739 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:11]=[CH:10][CH:9]=2)=[O:5])C.[OH-].[K+].CCO>>[CH2:16]([O:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]2)[CH:17]([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 668415224-Isobutoxy-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668416074-Isobutoxy-1H-indole-2-carboxylic acid

Procedure

4-Isobutoxy-1H-indole-2-carboxylic acid ethyl ester 81 (5.2 g, 19.9 mmol) is mixed with a 1M-solution of KOH in EtOH (99.5 ml, 99.5 mmol) and stirred for 24 hours. The solvent is then evaporated and the residue is partitioned between water and ether. The water layer is acidified with HCl and extracted twice with ether. The combined organic layers are washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give a beige powder.

Workup

  1. customThe solvent is then evaporated
  2. customthe residue is partitioned between water and ether
  3. extractionextracted twice with ether
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a beige powder

Sources & evidence

ORD record
ord-125838210e9b495da33b877fb302d1b6
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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