Methanol → HCID 70086888, compound

HRID 277094

Reaction equation

HRID 277094 reaction equation
[H-].[Na+].[Cl-].[C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:5].[F:26][C:27]1[CH:32]=[C:31]([CH:33]=O)[CH:30]=[CH:29][N:28]=1.CO>O1CCCC1.CN(C)C=O>[F:26][C:27]1[CH:32]=[C:31](/[CH:33]=[CH:6]\[C:4]#[N:5])[CH:30]=[CH:29][N:28]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 27629902-Fluoroisonicotinaldehyde

Product 1

HCID 70086888HCID 70086888, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.80 g (0.038 mol) sodiumhydride (60% in oil) in 120 ml tetrahydrofurane and 120 ml dimethylformamide were added 21.6 g (0.064 mol) (cyanomethyl)triphenyl-phosphonium chloride. After stirring for 1 hour at room temperature a solution of 4.00 g (0.032 mol) 2-fluoro-4-pyridinecarboxaldehyde in 35 ml tetrahydrofurane were added and stirring was continued for 2 days. Then 30 ml methanol were added, the solvents were evaporated and the residue chromatographed on silicagel with ethylacetate/hexane 1/2 to yield 0.45 g (10%) (E)-and (Z)-3-(2-fluoro-pyridin-4-yl)-acrylonitrile as light yellow solid. MS m/e (%): 148 (M+, 100), 128 (43).

Workup

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

Sources & evidence

ORD record
ord-f02a2b9941d84a9d8680f5f010cb72ca
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Linked notes

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