Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 19842224, compound

HRID 280543Notes

Reaction equation

HRID 280543 reaction equation
C([O:3][C:4]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])C.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:42](O)[C:41]3[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=3[C:35]2=[O:44])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH3:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([N:34]2[C:35](=[O:44])[C:36]3[CH2:37][CH2:38][CH2:39][CH2:40][C:41]=3[CH:42]2[CH2:6][C:4]([OH:5])=[O:3])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 12234949HCID 12234949, compound

Product 1

HCID 19842224HCID 19842224, compoundYield 948%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethoxycarbonylmethylenetriphenylphosphorane (3.0 g) was added to a solution of 2-(4-methoxyphenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolin-1-one (2.59 g) in toluene (30 ml) and the solution was refluxed gently for 48 hours. After cooling, the solvent was distilled off and the residue was dissolved in 30 ml of methanol. Potassium carbonate (3 g) and water (10 ml) were added and the mixture was refluxed for an hour. After cooling, the methanol was distilled off, 100 ml of water and 100 ml of dichloromethane were added and the mixture was stirred well. The aqueous layer was separated and acidified with 5% hydrochloric acid to give crystals, which were washed with water, dried and recrystallized from methanol-ether (1:3) to give 24.6 g of 2-(4-methoxyphenyl)-3-oxo-4,5,6,7-tetrahydroisoindoline-1-acetic acid.

Workup

  1. temperaturethe solution was refluxed gently for 48 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in 30 ml of methanol
  5. additionPotassium carbonate (3 g) and water (10 ml) were added
  6. temperaturethe mixture was refluxed for an hour
  7. temperatureAfter cooling
  8. distillationthe methanol was distilled off
  9. addition100 ml of water and 100 ml of dichloromethane were added
  10. customThe aqueous layer was separated
  11. customto give crystals, which
  12. washwere washed with water
  13. customdried
  14. customrecrystallized from methanol-ether (1:3)

Sources & evidence

ORD record
ord-7ed2250484664a24984d7402dd4e7c50
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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