Indole → 1-Octyl-1H-indole

HRID 1636193Notes

Reaction equation

HRID 1636193 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+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[CH2:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 798IndoleHCID 81401-BromooctaneHCID 14797Potassium Hydroxide

Product 1

HCID 128272731-Octyl-1H-indoleYield 72.3%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 241BenzeneSolvent2×

Procedure

A mixture of indole (1) (0.03 mole, 3.51 g), potassium hydroxide (0.03 mole, 1.97 g) powdered in a mortar, and 18-crown-6 ether (0.001 mole, 250 mg) in benzene (20 cm3) is heated under reflux with vigorous stirring for two hours. A solution of octylbromide (2a), (0.04 mole, 7.72 g) in benzene (10 cm3) is added and reflux is maintained for an additional four hours. The reaction is monitored by TLC and the reaction mixture is filtered on Celite. Evaporation of the solvent yields an orange liquid which is purified by distillation in vacuo. The colourless liquid distilled at 154-156° C. and 1.5 mmHg pressure is shown by 1H nmr to be pure 1-octylindole (3a) (4.98 g, 0.0217 mole, 72% yield).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturereflux
  4. temperatureis maintained for an additional four hours
  5. filtrationthe reaction mixture is filtered on Celite
  6. customEvaporation of the solvent
  7. customyields an orange liquid which
  8. distillationis purified by distillation in vacuo
  9. distillationThe colourless liquid distilled at 154-156° C.

Sources & evidence

ORD record
ord-3bbccff0c1224cf0bd606ae94d1e0e46
Source dataset
uspto-grants-2000_03
Patent number
US06033601

Reaction notes

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