4-Pyridinecarboxaldehyde → HCID 10352231, compound

HRID 1711135Notes

Reaction equation

HRID 1711135 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[C:9]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:11][CH2:12][CH3:13])=[O:10]>C1(C)C=CC=CC=1>[CH2:12]([O:11][C:9](=[O:10])/[CH:14]=[CH:7]/[C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[CH3:13]

Participants

4

Reactant 2

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

Product 1

HCID 10352231HCID 10352231, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-pyridinecarboxaldehyde (333 mg, 3.11 mmol) and (carboethoxy-methylene)triphenylphosphorane (1.19 g, 3.42 mmol) in toluene (8.0 ml) was stirred at 90° C. under nitrogen for 3 hours. Once cooled, the solvent was removed under reduced pressure, the crude product was acidified with 1M HCl (25 ml) and the solution was washed with Et2O (25 ml×2). The aqueous solution was made basic with 1M NaOH and extracted with CH2Cl2 (25 ml×2). The combined organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure, giving (E)-3-pyridin-4-yl-acrylic acid ethyl ester as a white solid (238 mg, 1.34 mmol, 43%). 1H NMR (CDCl3) δ 1.35 (t, 3H, J=7.2 Hz), 4.29 (q, 2H, J=7.2 Hz), 6.59 (d, 1H, J=16.2 Hz), 7.37 (d, 2H, J=6.1 Hz), 7.60 (d, 1H, J=16.2 Hz), 8.66 (d, 2H, J=6.1 Hz).

Workup

  1. temperatureOnce cooled
  2. customthe solvent was removed under reduced pressure
  3. washthe solution was washed with Et2O (25 ml×2)
  4. extractionextracted with CH2Cl2 (25 ml×2)
  5. dry with materialThe combined organic solution was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7131555288f24cbf9188d905688c78af
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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