4-Pyridinecarboxaldehyde → HCID 10352231, compound

HRID 1712923Notes

Reaction equation

HRID 1712923 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C1(P(=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[N:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 10352231HCID 10352231, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isonicotinaldehyde (0.811 mL, 8.61 mmol) in DCM (30 mL) was added ethyl (triphenylphosphoranylidene)acetate (3.00 g, 8.61 mmol) in DCM (5 mL) dropwise. The reaction mixture was allowed to stir at rt for 5 h and then concentrated. The residue was purified by column chromatography to give ethyl (2E)-3-pyridin-4-ylacrylate (1.47 g, 96%). LCMS: (FA) ES+ 178.3.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e85cd61bc6e3438e990dd6d0d07e6b85
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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