Indole → 4,4-di-(1H-indolyl-)butanoic acid
Reaktionsgleichung
[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]1Komponenten
4
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 35 °C
Versuchsvorschrift
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.
Aufarbeitung
- customAt the end of that period the methanol was removed under vacuum
- extractionthe residue was extracted with ethyl acetate (3×50 ml)
- washwashed with a small amount of water
- dry with materialdried on anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe end product was isolated
- custompurified chromatographically on an SiO2 column
Quellen und Nachweise
- ORD-Eintrag
- ord-ce562329315947d4a7330023ab1ce86c
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07084166B2
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