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

HRID 2267764Notes

Reaction equation

HRID 2267764 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-8b6b292c5ade4de4bdce5aa2efea04b4
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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