Citric Acid → {5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetic acid

HRID 1163322Notes

Reaction equation

HRID 1163322 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH2:26][C:27]([O:29]CC)=[O:28])[CH:21]=[CH:20]3)[CH:10]=1.CO.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.O1CCCC1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH2:26][C:27]([OH:29])=[O:28])[CH:21]=[CH:20]3)[CH:10]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 58755253ethyl {5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetate

Product 1

HCID 23111764{5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetic acidYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {5-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-1H-indol-1-yl}acetate (0.27 g, 0.65 mmol) in a mixed solvent of methanol (10 mL) and tetrahydrofuran (10 mL) was added 85% aqueous solution (5 mL) of potassium hydroxide (0.13 g, 1.97 mmol), and the mixture was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was made weak acidic with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2-2:1) to give the title compound (0.19 g, yield 76%) as a pale-yellow amorphous solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2-2:1)

Sources & evidence

ORD record
ord-fab6029b66e8438397929305197e182f
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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