Reaktion #2493847

ord-b1c0abd4039f4229a8120d64977fc0a5

Reaktionsgleichung

C[C@@H](CC(=O)Cl)CC(=O)OC[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
4-chlorocarbonyl-3-(R)-methyl-butyric acid (tert-butyl-diphenyl-silanyl)-methyl ester
CCCCCCc1cc2cc(Cl)ccc2n1C
5-chloro-2-hexyl-1-methyl-1H-indole
[CH3][Al+][CH3].[Cl-]
dimethyl aluminum chloride
→
CCCCCCc1cc2ccc(Cl)cc2n1C(=O)C[C@H](C)CC(=O)OC[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
5-(6-Chloro-2-hexyl-indol-1-yl)-3-(S)-methyl-5-oxo-pentanoic acid (tert-butyl-diphenyl-silanyl)-methyl ester

Edukte

C[C@@H](CC(=O)Cl)CC(=O)OC[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
4-chlorocarbonyl-3-(R)-methyl-butyric acid (tert-butyl-diphenyl-silanyl)-methyl ester
CCCCCCc1cc2cc(Cl)ccc2n1C
5-chloro-2-hexyl-1-methyl-1H-indole
[CH3][Al+][CH3].[Cl-]
dimethyl aluminum chloride

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGstirred for 3 hours
  2. 2
    SonstigeThe reaction was quenched with saturated ammonium chloride solution
  3. 3
    Extraktionextracted with ethyl acetate
  4. 4
    SonstigeThe product was purified by column chromatography

Vorschrift

To the solution of 5-chloro-2-hexyl-1-methyl-1H-indole in methylene chloride was added dimethyl aluminum chloride at 0 0 C and was stirred for 60 minutes. Then to this mixture, 4-chlorocarbonyl-3-(R)-methyl-butyric acid (tert-butyl-diphenyl-silanyl)-methyl ester was added and 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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08809382B2uspto-grants-2014_08