Indole → 1-Octyl-1H-indole

HRID 1611403Notes

Reaction equation

HRID 1611403 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+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].O>CS(C)=O>[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 4

HCID 798IndoleHCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydride

Product 1

HCID 128272731-Octyl-1H-indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of indole (1.0 g) in dry DMSO (1 ml) is dropped into a suspension of sodium hydride (60% suspension in mineral oil; 0.37 g) in dry DMSO (20 ml), heating to 60° C. for 1 h. After cooling at room temperature, the resulting solution is added dropwise with a solution of n-octyl bromide (2.82 ml) in dry DMSO (2.8 ml). After a night at room temperature, the reaction mixture is poured into water (200 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phases are washed with a NaCl saturated solution, dried and evaporated to dryness. The resulting residue is purified by column chromatography (silica gel; eluent n-hexane) to obtain 1.86 g of 1-(n-octyl)indole as oil.

Workup

  1. temperatureAfter cooling at room temperature
  2. waitAfter a night at room temperature
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic phases are washed with a NaCl saturated solution
  5. customdried
  6. customevaporated to dryness
  7. customThe resulting residue is purified by column chromatography (silica gel; eluent n-hexane)

Sources & evidence

ORD record
ord-047f1d28e35649159ae8b1dc2377d6b9
Source dataset
uspto-grants-2006_01
Patent number
US06987122B2

Reaction notes

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