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

HRID 277022Notes

Reaction equation

HRID 277022 reaction equation
[H-].[Na+].[Cl-].[C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:5].[CH:26]([C:29]1[CH:34]=[C:33]([CH:35]=O)[CH:32]=[CH:31][N:30]=1)([CH3:28])[CH3:27].CO>O1CCCC1.CN(C)C=O>[CH:26]([C:29]1[CH:34]=[C:33]([CH:35]=[CH:6][C:4]#[N:5])[CH:32]=[CH:31][N:30]=1)([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 183135762-Isopropylisonicotinaldehyde

Product 1

HCID 700882473-(2-Isopropyl-pyridin-4-yl)-acrylonitrileYield 11.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 6.55 g (0.15 mol) sodiumhydride in 220 ml tetrahydrofurane and 220 ml dimethylformamide were added 50.7 g (0.15 mol) (cyanomethyl)triphenylphosphonium chloride. After sirring for 1 hour at room temperature a solution of 22.4 g (0.15 mol) 2-isopropyl-4-pyridinecarboxaldehyde in 50 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 2.96 g 3-(2-isopropyl-pyridin-4-yl)-acrylonitrile as coorless oil. MS m/e (%): 172 (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-7134f50ea64a43079d118db321dd3cef
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

Loading…