Potassium Hydroxide → 5-(2-Hexyl-indol-1-yl)-3-methyl-5-oxo-pentanoic acid

HRID 2406631Notes

Reaction equation

HRID 2406631 reaction equation
[CH2:1]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[CH3:18][CH:19]1[CH2:24][C:23](=[O:25])[O:22][C:21](=[O:26])[CH2:20]1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[CH2:1]([C:7]1[N:8]([C:23](=[O:25])[CH2:24][CH:19]([CH3:18])[CH2:20][C:21]([OH:26])=[O:22])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 778283-Methylglutaric anhydrideHCID 14299246HCID 14299246, compound

Product 1

HCID 498045775-(2-Hexyl-indol-1-yl)-3-methyl-5-oxo-pentanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hexyl-1H-indole in DMSO was added KOH at RT and was stirred for 30 minutes. Then to this mixture, 4-methyl-dihydro-pyran-2,6-dione was added and stirred for 3 hours. The reaction was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-a5385f93eff24fab92e9c7d9c59144a6
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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