3-Pyridinecarboxaldehyde → 4-(Pyridin-3-yl)but-3-en-2-one

HRID 1249321Notes

Reaction equation

HRID 1249321 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:16][C:17](=[O:19])[CH3:18])C=CC=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:16][C:17](=[O:19])[CH3:18])[CH:2]=1

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 150381-(Triphenylphosphoranylidene)acetone

Product 1

HCID 27779424-(Pyridin-3-yl)but-3-en-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyridine-3-carboxaldehyde (18.9 ml) and 1-triphenylphosphoranylidene-2-propanone (70 g) were heated at reflux in toluene for 2 hr. The solvent was evaporated and the residue was distilled at reduced pressure to give 1-(3-pyridyl)but-1-en-3-one as an oil. Pmr spectrum (CDCl3 ; δ in ppm): 2.41 (3H, s); 6.79 (1H, d); 7.2-8.77 (4H, m); 7.52 (1H, d).

Workup

  1. customThe solvent was evaporated
  2. distillationthe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-fdba032fb1ab4c3b81626914406b07f2
Source dataset
uspto-grants-1986_12
Patent number
US04631081

Reaction notes

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