Methanol → HCID 22629694, compound

HRID 277096Notes

Reaction equation

HRID 277096 reaction equation
[H-].[Na+].[Cl-].[PH4+].[C:5]([CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:6].[Cl-].[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([CH:35]=O)=[N:33][CH:34]=1.CO>O1CCCC1.CN(C)C=O>[Cl:28][C:29]1[CH:30]=[CH:31][C:32](/[CH:35]=[CH:7]/[C:5]#[N:6])=[N:33][CH:34]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 101032675-Chloropyridine-2-carboxaldehydeHCID 86757849HCID 86757849, compound

Product 1

HCID 22629694HCID 22629694, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.97 g, (0.045 mol) sodiumhydride (60% in oil) in 60 ml tetrahydrofurane and 60 ml dimethylformamide were added 15.25 g (0.045 mol) (cyanomethyl)triphenyl-phosphonium phosphonium chloride. After stirring for 1 hour at room temperature a solution of 6.39 g (0.045 mol) 5-chloro-2-pyridinecarboxaldehyde in 25 ml tetrahydrofurane were added and stirring was continued for 2 days. Then 15 ml methanol were added, the solvents were evaporated and the residue was chromatographed on aluminiumoxide with ethylacetate/hexane 3/7 to yield 4.09 g (55%) (E)-3-(5-chloro-pyridin-2-yl)-acrylonitrile as white solid. MS m/e (%): 164 (M30 , 100), 137 (17), 113 (45).

Workup

  1. additionwere added
  2. customthe solvents were evaporated
  3. customthe residue was chromatographed on aluminiumoxide with ethylacetate/hexane 3/7

Sources & evidence

ORD record
ord-07662fa505644ead9e946f9936df6858
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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