Sodium hydride → 4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamonitrile

HRID 233278

Reaktionsgleichung

Reaktionsgleichung von HRID 233278
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH2:26][CH2:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1>O1CCCC1>[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH2:26][CH2:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[CH:5][C:3]#[N:4])=[CH:31][CH:30]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Produkt 1

HCID 536629724-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamonitrileAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil, 2.0 g) was added, in small portions at 0° C. a solution of diethyl cyanomethylphosphonate (8.2 g) in tetrahydrofuran (150 ml). The mixture was stirred for about 15 minutes, to which was added 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (13.0 g), and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off to leave 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamonitrile (11.8 g, 85%). The product was recrystallized from ethyl acetate--hexane to give colorless needles, m.p.112°-113° C.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-12d6a4b2e7c5455cb01963c85d03fe6b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591862

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