Indole → HCID 58088558, Verbindung

HRID 250191

Reaktionsgleichung

Reaktionsgleichung von HRID 250191
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([O:20][CH3:21])(=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].O>CN(C=O)C>[CH3:21][O:20][C:10](=[O:19])[CH2:11][CH:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 637520Methyl Cinnamate

Produkt 1

HCID 58088558HCID 58088558, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of indole (2.88 g, 25 mmol) and methyl trans-cinnamate (3.98 g, 25 mmol) in anhydrous DMF (50 mL) was added a suspension of 60% NaH (0.29 g, 7 mmol) at room temperature. The reaction mixture was allowed to stir for 6 hours at room temperature. The reaction mixture was poured into water (300 mL) and product was extracted with EtOAc (2×200 mL). The combined organic extracts were washed with water (5×200 ml), dried over Na2SO4 and evaporated under vacuum. Purification by chromatography (SiO2, benzene-hexane, 1:9) afforded 1.51 g (22% yield) of 3-indol-1-yl-3-phenyl-propionic acid methyl ester as a white powder: MS 280 (M+H)+.

Aufarbeitung

  1. extractionwas extracted with EtOAc (2×200 mL)
  2. washThe combined organic extracts were washed with water (5×200 ml)
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum
  5. customPurification by chromatography (SiO2, benzene-hexane, 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-db4d95b25a1a405c8ba3d4feb411d844
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863305B2

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