Water → HCID 54327211, compound

HRID 1060004Notes

Reaction equation

HRID 1060004 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[C:24]([N+:30]([O-:32])=[O:31])[CH:23]=2)[CH:17]=1.O>O1CCCC1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[CH:29]=[CH:28][C:25]([CH:26]=[CH:5][C:3]#[N:4])=[C:24]([N+:30]([O-:32])=[O:31])[CH:23]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 186675454-(4-Methoxypyridin-2-yl)-2-nitrobenzaldehyde

Product 1

HCID 54327211HCID 54327211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 192 mg) in tetrahydrofuran (10 ml) was added a solution of diethyl cyanomethylphosphonate (0.777 ml) dropwise at 0° C., and the mixture was stirred at ambient temperature for 30 minutes. Then to the resultant mixture was added a solution of 4-(4-methoxypyridin-2-yl)-2-nitrobenzaldehyde (1.03 g) in tetrahydrofuran (20 ml) dropwise at 0° C., and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, filtered and dried to give 4-(4-methoxypyridin-2-yl)-2-nitrocinnamonitrile (1.11 g) as a mixture of regioisomers.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with diisopropyl ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-a69682d02c1548a0b54aa38cdace9267
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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