Glutaric anhydride → 5-(2-Hex-1-enyl-indol-1-yl)-5-oxo-pentanoic acid

HRID 2406627Notes

Reaction equation

HRID 2406627 reaction equation
[CH:1]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].[O:18]1[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]1=[O:25].[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[CH:1]([C:7]1[N:8]([C:23](=[O:24])[CH2:22][CH2:21][CH2:20][C:19]([OH:25])=[O:18])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 7940Glutaric anhydrideHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 666441492-Hex-1-enyl-1H-indole

Product 1

HCID 666442675-(2-Hex-1-enyl-indol-1-yl)-5-oxo-pentanoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hex-1-enyl-1H-indole in DMSO was added KOH at RT and this was stirred for 30 minutes. Dihydro-pyran-2,6-dione was added to the reaction mixture 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-7b00a14085534980960298f724de382a
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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