Indole → 1-[(2,4,6-Trimethylphenyl)methyl]-1H-indole

HRID 353470

Reaktionsgleichung

Reaktionsgleichung von HRID 353470
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:12][C:13]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:14]=1[CH2:15]Cl.O>CS(C)=O>[CH3:12][C:13]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:14]=1[CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 741082,4,6-Trimethylbenzyl chloride

Produkt 1

HCID 222567421-[(2,4,6-Trimethylphenyl)methyl]-1H-indoleAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of indole (1.185 g) in dry DMSO (3 ml) is dropped into a suspension of sodium hydride (60% mineral oil suspension; 0.44 g) in dry DMSO (10 ml). After two hours, the resulting solution is added with a solution of 2,4,6-trimethylbenzyl chloride (1.9 g) in dry DMSO (2 ml) heating at 60° C. for 6 h. The reaction mixture is kept at room temperature overnight, then poured into water (250 ml) extracted with ethyl acetate and dried (Na2SO4). The drying agent is filtered off, the solvent is evaporated off under reduced pressure and the resulting residue is purified by column chromatography (silica gel; eluent n-hexane/AcOEt 9/1) to obtain 2.2 g of 1-(2,4,6-trimethylbenzyl)indole.

Aufarbeitung

  1. waitThe reaction mixture is kept at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationThe drying agent is filtered off
  5. customthe solvent is evaporated off under reduced pressure
  6. customthe resulting residue is purified by column chromatography (silica gel; eluent n-hexane/AcOEt 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-879af4c043fb407ea9d2fc46a8361995
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753342B2

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