Indole → 1-(4-Ethylbenzyl)-1H-indole

HRID 554574Notes

Reaction equation

HRID 554574 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=1>C(O)C>[CH2:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:15][CH:16]=1)[CH3:21]

Participants

5

Reactant 3

HCID 798IndoleHCID 14797Potassium HydroxideHCID 738434-Ethylbenzyl chloride

Product 1

HCID 638117451-(4-Ethylbenzyl)-1H-indoleYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of indole (4.0 g, 34.1 mmol), potassium hydroxide (2.40 g, 42.6 mmol) in ethanol (200 mL) was added and the mixture solution was stirred at room temperature for two hours. The solvent was distilled under reduced pressure. The residue was dissolved in acetone (200 mL), and 1-chloromethyl-4-ethylbenzene (5.28 g, 34.1 mmol) was added thereto. The reaction mixture was stirred at room temperature a whole day and night, and then subjected to Celite filtration and the filtrate was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:500)] to obtain the title compound (3.8 g, 47%).

Workup

  1. distillationThe solvent was distilled under reduced pressure
  2. dissolutionThe residue was dissolved in acetone (200 mL)
  3. stirringThe reaction mixture was stirred at room temperature a whole day and night
  4. filtrationsubjected to Celite filtration
  5. distillationthe filtrate was distilled under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:500)]

Sources & evidence

ORD record
ord-9b9e71ba725049fcb90caa488109bc0f
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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