Water → HCID 66841602, compound

HRID 1929027Notes

Reaction equation

HRID 1929027 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([O:14][CH:15]([CH3:17])[CH3:16])[CH:10]=[CH:9][CH:8]=2)=[O:4].[Li+].[OH-].O>C1COCC1>[CH: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)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66841425methyl 4-(2-propoxy)-1H-indole-2-carboxylate

Product 1

HCID 66841602HCID 66841602, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Isopropoxy-1H-indole-2-carboxylic acid methyl ester 76 (114 mg, 0.49 mmol) is dissolved in 5 ml of THF. A 2M-solution of LiOH in water (2.5 ml, 5 mmol) is added and the mixture is stirred for 48 hours. The solvent is then evaporated and the residue is partitioned between water and EtOAc. 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 EtOAc
  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-f861786c00bd466f9cdd107182df21bd
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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