Indole → Ethyl 4-(1H-indol-1-yl)butanoate

HRID 1034059Notes

Reaction equation

HRID 1034059 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:1]1([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 19024819Ethyl 4-(1H-indol-1-yl)butanoateYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of indole (11.7 g), ethyl 4-bromobutyrate (58.5 g) and potassium carbonate (41.5 g) in N,N-dimethylformamide (500 ml) was heated at 50° C. for 10 hours. The mixture was filtered and the filtrate was poured into a mixture of ethyl acetate and ice water. The organic layer was separated, washed with water, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (1 kg) eluting with a mixture of methanol, chloroform and hexane (1:50:50) to give ethyl 4-(1-indolyl)butyrate (2.86 g) as a blue oil.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was poured into a mixture of ethyl acetate and ice water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was chromatographed on silica gel (1 kg)
  8. washeluting with a mixture of methanol, chloroform and hexane (1:50:50)

Sources & evidence

ORD record
ord-262cd0f72ff8423caecc90b1f9a411f8
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Reaction notes

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