Potassium Carbonate → 2-[3-(4-Methoxy-phenyl)-2-methyl-1-propyl-1H-indole-5-yloxy]-2-methylpropanoic acid

HRID 66889

Reaction equation

HRID 66889 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=3)[N:11]([CH2:19][CH2:20][CH3:21])[C:10]=2[CH3:22])=[CH:5][CH:4]=1.Br[C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=[O:26])[CH:16]=3)[N:11]([CH2:19][CH2:20][CH3:21])[C:10]=2[CH3:22])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 749242-Bromo-2-methylpropanoic acidHCID 205291893-(4-methoxyphenyl)-2-methyl-1-propyl-1H-indole-5-ol

Product 1

HCID 205290812-[3-(4-Methoxy-phenyl)-2-methyl-1-propyl-1H-indole-5-yloxy]-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.9 g (0.02 mole) of 3-(4-methoxyphenyl)-2-methyl-1-propyl-1H-indole-5-ol, 5.1 g (0.03 mole) of 2-bromo-2-methyl-propanoic acid, and 15 g of potassium carbonate was refluxed in 100 ml of acetone for 48 hours. The acetone was removed in vacuo, and the residue was acidified with 2N hydrochloric acid. After extraction with ethyl acetate, the extracts were dried over sodium sulfate and evaporated. The residue obtained was purified by chromatography on silicagel (eluant: chloroform/methanol (9:1)).

Workup

  1. customThe acetone was removed in vacuo
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialthe extracts were dried over sodium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on silicagel (eluant: chloroform/methanol (9:1))

Sources & evidence

ORD record
ord-acfe4b0ec0cf4652b3bbfe920251e012
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Linked notes

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