Methanol → (E)-3-(2-ethyl-pyridin-4-yl)-acrylonitrile

HRID 277018Notes

Reaction equation

HRID 277018 reaction equation
[H-].[Na+].[Cl-].[C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:5].[CH2:26]([C:28]1[CH:33]=[C:32]([CH:34]=O)[CH:31]=[CH:30][N:29]=1)[CH3:27].CO>O1CCCC1.CN(C)C=O>[CH2:26]([C:28]1[CH:33]=[C:32](/[CH:34]=[CH:6]/[C:4]#[N:5])[CH:31]=[CH:30][N:29]=1)[CH3:27]

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 120261252-Ethyl-4-pyridinecarboxaldehyde

Product 1

HCID 22629691(E)-3-(2-ethyl-pyridin-4-yl)-acrylonitrileYield 25.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.79 g (0.041 mol) sodiumhydride in 50 ml tetrahydrofurane and 50 ml dimethylformamide were added 13.9 g (0.041 mol) (cyanomethyl)triphenylphosphonium chloride. After sirring for 1 hour at room temperature a solution of 5.54 g (0.041 mol) 2-ethyl-4-pyridinecarboxaldehyde in 10 ml tetrahydrofuran were added and stirring was continued for 15 hours. Then 10 ml methanol were added, the solvents were evaporated and the residue chromatographed on aluminiumoxide with dichloromethane to yield 1.63 g (25%) (E)-3-(2-ethyl-pyridin-4-yl)-acrylonitrile as white waxy solid. MS m/e (%): 158 (M+, 100).

Workup

  1. waitwas continued for 15 hours
  2. customthe solvents were evaporated
  3. customthe residue chromatographed on aluminiumoxide with dichloromethane

Sources & evidence

ORD record
ord-12ddcac05ed943aeaa02421b8e728d19
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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