Water → HCID 11046131, compound

HRID 233290Notes

Reaction equation

HRID 233290 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][O:27][C:28]1[CH:37]=[CH:36][C:31]([CH:32]=[CH:33][CH:34]=O)=[CH:30][CH:29]=1.O>O1CCCC1>[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:17][C:16]=1[CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:31](/[CH:32]=[CH:33]/[CH:34]=[CH:5]/[C:3]#[N:4])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 53888831HCID 53888831, compound

Product 1

HCID 11046131HCID 11046131, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 0.32 g) was added, in small portions at 0° C., to a solution of diethyl cyanomethylphosphonate (1.3 g) in tetrahydrofuran (50 ml). The mixture was stirred for 15 minutes at the same temperature, to which was then added 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamoaldehyde (2.0 g), followed by stirring for 30 minutes under ice-cooling. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), which was then concentrated to give (E,E)-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2,4-pentadienenitrile (1.5 g, 68%). Recrystallization of the product from ethyl acetate--hexane afforded colorless needles, m.p.120°-121° C.

Workup

  1. stirringby stirring for 30 minutes under ice-
  2. temperaturecooling
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4), which
  6. concentrationwas then concentrated

Sources & evidence

ORD record
ord-1012e6975189454482bf819935c6a8de
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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