Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 54238850, compound

HRID 990724Notes

Reaction equation

HRID 990724 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13]>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12](=[O:13])/[CH:14]=[CH:8]/[C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 54238850HCID 54238850, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-methylpyridine-3-carboxaldehyde (2 g, 16.5 mmol) and methyl (triphenylphosphoranylidene) acetate (6.1 g, 1.1 eq.) in toluene (100 mL) was stirred at reflux for 18 hours. The solvent was removed in vacuo, the residue washed with diethyl ether (100 mL) and filtered. The crude product was purified by chromatography eluting with CH2Cl2/MeOH (99/1) to give the title compound as a white solid (2.47 g, 85%). 1H NMR (CDCl3, 250 MHZ) δ(ppm); 8.60 (d, 1H); 7.70 (dd, 1H); 7.65 (d, J=15 Hz, 1H); 7.20 (d, 1H); 6.50 (d, J=15 Hz, 1H); 3.85 (s, 3H); 2.60 (s, 3H).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue washed with diethyl ether (100 mL)
  4. filtrationfiltered
  5. customThe crude product was purified by chromatography
  6. washeluting with CH2Cl2/MeOH (99/1)

Sources & evidence

ORD record
ord-c4d86b3ed6aa490e9c2465a64d7a0f0e
Source dataset
uspto-grants-2002_10
Patent number
US06462047B1

Reaction notes

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