2-(2-(4-(4-Fluorophenoxy)-2-propylphenoxy)-ethyl)-indole-5-acetate → 2-(2-(4-(4-Fluorophenoxy)-2-propyl phenoxy)ethyl)-indole-5-acetic acid

HRID 1057816Notes

Reaction equation

HRID 1057816 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][C:14]3[NH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][C:19]([CH2:23][C:24]([O-:26])=[O:25])=[CH:18][CH:17]=4)=[C:9]([CH2:29][CH2:30][CH3:31])[CH:8]=2)=[CH:4][CH:3]=1>CO.[Li+].[OH-]>[F:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH2:13][C:14]3[NH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][C:19]([CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=4)=[C:9]([CH2:29][CH2:30][CH3:31])[CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 186724922-(2-(4-(4-Fluorophenoxy)-2-propylphenoxy)-ethyl)-indole-5-acetate

Product 1

HCID 154857512-(2-(4-(4-Fluorophenoxy)-2-propyl phenoxy)ethyl)-indole-5-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

A solution of 2-(2-(4-(4-fluorophenoxy)-2-propylphenoxy)-ethyl)-indole-5-acetate (mg, mmol) in MeOH (mL) and LiOH (mL) was heated at reflux for 3 hours. The mixture was acidified to pH 6 with 1 N HCL and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound.

Workup

  1. temperatureat reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-802a0c18931c405c99e1889930c490cc
Source dataset
uspto-grants-2003_02
Patent number
US06515015B1

Reaction notes

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