Methanol → 3-(2-Propyl-pyridin-4-yl)-acrylonitrile

HRID 277020Notes

Reaction equation

HRID 277020 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:29]1[CH:34]=[C:33]([CH:35]=O)[CH:32]=[CH:31][N:30]=1)[CH2:27][CH3:28].CO>O1CCCC1.CN(C)C=O>[CH2:26]([C:29]1[CH:34]=[C:33]([CH:35]=[CH:6][C:4]#[N:5])[CH:32]=[CH:31][N:30]=1)[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 226296632-Propyl-4-pyridinecarboxaldehyde

Product 1

HCID 700871883-(2-Propyl-pyridin-4-yl)-acrylonitrileYield 46.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.39 g (0.03 mol) sodiumhydride in 40 ml tetrahydrofurane and 40 ml dimethylformamide were added 10.13 g (0.03 mol) (cyanomethyl)triphenylphosphonium chloride. After sirring for 1 hour at room temperature a solution of 4.48 g (0.03 mol) 2-propyl-4-pyridinecarboxaldehyde in 15 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 2.42 g 3-(2-propyl-pyridin-4-yl)-acrylonitrile as yellow oil. MS m/e (%): 173 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-eb89275c9cdb42e8abfba864d3e39d48
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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