Butanal → HCID 19610404, Verbindung

HRID 1602109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602109
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH:12]=O.[CH:14](=[O:18])[CH2:15][CH2:16][CH3:17].C(OC(C)C)(C)C>O.CCO>[CH2:16](/[C:15](=[CH:12]\[C:4]1[NH:3][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)/[CH:14]=[O:18])[CH3:17]

Komponenten

7

Edukt 4

HCID 261ButanalHCID 7914Diisopropyl EtherHCID 14797Potassium HydroxideHCID 96389Indole-2-carboxaldehyde

Produkt 1

HCID 19610404HCID 19610404, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of KOH pellets (0.4 g, 7.1 mmol) in H2O (5 ml), indole-2-carboxaldehyde (0.5 g, 3.44 mmol) in EtOH (45 ml) was added. After cooling to 0° C. butyraldehyde (0.31 ml, 3.44 mmol) was added and the reaction mixture was stirred at room temperature for 12 h. The ethanol was removed under vacuum and the aqueous solution was adjusted to pH 5 and extracted with EtOAc (3×10 ml). The combined organic layers were washed with brine (10 ml), dried over Na2SO4 and evaporated under vacuum. The residue was purified by flash-chromatography (hexane/EtOAc 7:3) to afford, after trituration with isopropyl ether, 0.3 g (44%) of the title compound.

Aufarbeitung

  1. additionwas added
  2. customThe ethanol was removed under vacuum
  3. extractionextracted with EtOAc (3×10 ml)
  4. washThe combined organic layers were washed with brine (10 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum
  7. customThe residue was purified by flash-chromatography (hexane/EtOAc 7:3)
  8. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-d38154107c59484f9425a2b0937e044d
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05981525

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