Potassium Hydroxide → 3-Methyl-5-(2-octyl-indol-1-yl)-5-oxo-pentanoic acid

HRID 2406651Notes

Reaction equation

HRID 2406651 reaction equation
[CH2:1]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[K+].[CH3:20][CH:21]1[CH2:26][C:25](=[O:27])[O:24][C:23](=[O:28])[CH2:22]1.[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[CH3:20][CH:21]([CH2:26][C:25]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:9]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:27])[CH2:22][C:23]([OH:28])=[O:24]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 778283-Methylglutaric anhydrideHCID 10889703HCID 10889703, compound

Product 1

HCID 666441163-Methyl-5-(2-octyl-indol-1-yl)-5-oxo-pentanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-octyl-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 mixture 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-61204373137e4124a4b37873f4e0c7b7
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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