3-Methylglutaric anhydride → 5-(5-Chloro-2-heptyl-1-methyl-1H-indol-3-yl)-3-methyl-5-oxo-pentanoic acid

HRID 2406676Notes

Reaction equation

HRID 2406676 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:5]2.[Cl-].C[Al+]C.[CH3:23][CH:24]1[CH2:29][C:28](=[O:30])[O:27][C:26](=[O:31])[CH2:25]1>C(Cl)Cl.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:5]2[C:28](=[O:30])[CH2:29][CH:24]([CH3:23])[CH2:25][C:26]([OH:31])=[O:27]

Participants

6

Reactant 3

HCID 778283-Methylglutaric anhydrideHCID 16686359Dimethylalumanylium chlorideHCID 687494535-Chloro-2-heptyl-1-methyl-1H-indole

Product 1

HCID 498023175-(5-Chloro-2-heptyl-1-methyl-1H-indol-3-yl)-3-methyl-5-oxo-pentanoic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To the solution of 5-chloro-2-heptyl-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 4-methyl-dihydro-pyran-2,6-dione was added at 0° C. and the reaction mixture was stirred for 3 hours. The reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-d434c9017bd24670814e91de35def895
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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