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

HRID 233278

Reaction equation

HRID 233278 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-12d6a4b2e7c5455cb01963c85d03fe6b
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Linked notes

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