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

HRID 1611402Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of indole (1.185 g) in dry DMSO (3 ml) is dropped into a suspension of sodium hydride (60% suspension in mineral oil; 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) and the reaction mixture is heated at 60° C. for 6 h. After a night at room temperature, the reaction mixture is poured into water (250 ml) and extracted with ethyl acetate, then dried (Na2SO4) The drying agent is filtered off and the solvent is evaporated off under reduced pressure. 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.

Workup

waitAfter a night at room temperature
extractionextracted with ethyl acetate
dry with materialdried (Na2SO4) The drying agent
filtrationis filtered off
customthe solvent is evaporated off under reduced pressure
customThe resulting residue is purified by column chromatography (silica gel; eluent n-hexane/AcOEt 9/1)

Sources & evidence

ORD record: ord-e44e5c0371864af49c1dfd1a377acad9
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06987122B2

Reaction notes

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