Water → 4-(2,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid

HRID 1929062Notes

Reaction equation

HRID 1929062 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([O:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[CH:9][CH:8]=2)=[O:4].[Li+].[OH-].O>C1COCC1>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][O:14][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[NH:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 668412144-(2,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 668415364-(2,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2,2-Dimethyl-propoxy)-1H-indole-2-carboxylic acid methyl ester 90 (270 mg, 1.03 mmol) is dissolved in 20 ml of THF. A 2M-solution of LiOH in water (5.2 ml, 11 mmol) is added and the mixture is stirred for 48 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 EtOAc. The combined organic layers are washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give a yellow powder.

Workup

  1. customThe solvent is then evaporated
  2. customthe residue is partitioned between water and ether
  3. extractionextracted twice with EtOAc
  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 yellow powder

Sources & evidence

ORD record
ord-f0b68f577d414c42bcf0bec4b1da103a
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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