Veratraldehyde → HCID 54345694, Verbindung

HRID 235045

Reaktionsgleichung

Reaktionsgleichung von HRID 235045
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]#[N:24])=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22](=[CH:6][C:5]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:23]#[N:24])=[CH:14]1

Komponenten

5

Edukt 3

HCID 8419VeratraldehydeHCID 11430Potassium CarbonateHCID 351795Indole-3-acetonitrile

Produkt 1

HCID 54345694HCID 54345694, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2.0 g (12.0 mmole) 3,4 dimethoxybenzaldehyde in 75 ml absolute ethanol are added 2.07 g (13.3 mmole) 3-indolylacetonitrile and 1.83 g (13.3 mmole) anhydrous potassium carbonate. The reaction flask is equipped with a condenser and a drying tube (using anhydrous CaSO4), and the reaction was stirred and heated. After refluxing for 24 hours, the reaction is allowed to cool to room temperature. The reaction mixture is filtered to remove the salts, and the solvent is removed by rotary evaporation. The residue is purified by flash chromatography on silica gel, eluting with hexane-ethyl acetate, 3:1. The yellow solid is recrystallized from acetone-hexane to give 2-(3-indolyl)-3-(3,4-dimethoxy-phenyl)-2-propenenitrile, m.p. 139°-141° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureAfter refluxing for 24 hours
  3. filtrationThe reaction mixture is filtered
  4. customto remove the salts
  5. customthe solvent is removed by rotary evaporation
  6. customThe residue is purified by flash chromatography on silica gel
  7. washeluting with hexane-ethyl acetate, 3:1
  8. customThe yellow solid is recrystallized from acetone-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b0922b3823046768cd550f62dffee57
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597837

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