Sodium hydride → (E)-3-(1H-Indol-7-yl)acrylonitrile

HRID 54526

Reaktionsgleichung

Reaktionsgleichung von HRID 54526
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH:23]=O)[CH:16]=[CH:15]1>O1CCCC1.C(OCC)(=O)C>[C:3](/[CH:5]=[CH:23]/[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[NH:14][CH:15]=[CH:16]2)#[N:4]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2734629Indole-7-carboxaldehyde

Produkt 1

HCID 19959103(E)-3-(1H-Indol-7-yl)acrylonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride, 60% dispersion in mineral oil (0.10 g, 2.5 mmol) is added in portions over 10 minutes to a stirred solution of diethyl cyanomethylphosphonate (0.44 g, 2.5 mmol) in tetrahydrofuran (10 ml) cooled in ice. The mixture is stirred for 15 minutes then a solution of 7-indole carboxaldehyde (0.30 g, 2.1 mmol) in tetrahydrofuran (2 ml) is added dropwise. The mixture is stirred for 30 minutes, diluted with ethyl acetate, washed with water, dried and evaporated. The residue is chromatographed on silica in ethyl acetate-hexane (1:3) to give the product.

Aufarbeitung

  1. temperaturecooled in ice
  2. stirringThe mixture is stirred for 30 minutes
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on silica in ethyl acetate-hexane (1:3)
  7. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-28339c89712f412387a749f34ff15d9b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622969

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