Glutaric anhydride → 5-(2-Hexyl-1-methyl-1H-indol-3-yl)-5-oxo-pentanoic acid

HRID 2406645Notes

Reaction equation

HRID 2406645 reaction equation
[CH2:1]([C:7]1[N:8]([CH3:16])[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].[Cl-].C[Al+]C.[O:21]1[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C:22]1=[O:28].[Cl-].[NH4+]>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH2:1]([C:7]1[N:8]([CH3:16])[C:9]2[C:14]([C:15]=1[C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C:22]([OH:28])=[O:21])=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

8

Reactant 4

HCID 7940Glutaric anhydrideHCID 25517Ammonium ChlorideHCID 152139612-Hexyl-1-methyl-1H-indoleHCID 16686359Dimethylalumanylium chloride

Product 1

HCID 498045805-(2-Hexyl-1-methyl-1H-indol-3-yl)-5-oxo-pentanoic acid

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hexyl-1-methyl-1H-indole in methylene chloride at 0° C. was added dimethyl aluminum chloride solution in hexane. The reaction mixture was stirred for 30 minutes. To this solution dihydro-pyran-2,6-dione was added at 0° C. and the reaction mixture was stirred for 3 hours. The reaction was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-89cce1339ac74a27bf3c1f8266cd0ad0
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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