Indole → 4,4-di-(1H-indolyl-)butanoic acid

HRID 6946Notes

Reaction equation

HRID 6946 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH2:10]>CO>[N:1]1([CH:2]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:3][CH2:4][C:5]([OH:10])=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 798IndoleHCID 962Water

Product 1

HCID 220193114,4-di-(1H-indolyl-)butanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

282 mg of indole (2.4 mmol) were dissolved in 10 ml of CH3OH and 5 ml of H2O; 102 mg of semisuccinic aldehyde (1 mmol) and 240 mg of dysprosium triflate-(CF3SO3)3Dy-(0.393 mmol) were added. The resulting solution was stirred at 35° C. for 24 hours. At the end of that period the methanol was removed under vacuum and the residue was extracted with ethyl acetate (3×50 ml). The organic extracts were pooled, washed with a small amount of water, dried on anhydrous Na2SO4, filtered and concentrated to dryness. The end product was isolated and purified chromatographically on an SiO2 column, using a hexane:isopropyl alcohol gradient ranging from 9:1 to 8:2.

Workup

  1. customAt the end of that period the methanol was removed under vacuum
  2. extractionthe residue was extracted with ethyl acetate (3×50 ml)
  3. washwashed with a small amount of water
  4. dry with materialdried on anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe end product was isolated
  8. custompurified chromatographically on an SiO2 column

Sources & evidence

ORD record
ord-ce562329315947d4a7330023ab1ce86c
Source dataset
uspto-grants-2006_08
Patent number
US07084166B2

Reaction notes

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