Toluene → HCID 67482413, compound

HRID 2402288Notes

Reaction equation

HRID 2402288 reaction equation
O[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]=1.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14]CC)=[O:13].[C:37](=O)([O-])[O-:38].[K+].[K+].[C:43]1([CH3:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CCO.O>[CH3:37][O:38][C:46]1[CH:47]=[CH:48][C:43]([CH2:49][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:2]2[CH2:17][C:12]([OH:14])=[O:13])=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 178518309HCID 178518309, compound

Product 1

HCID 67482413HCID 67482413, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of the hydroxy isoindolone prepared in Part B (6.3 g, 0.023 mmol) and (carbethoxymethylene)-triphenylphosphorane (9.8 g, 28.1 mmol) in toluene (100 mL) was stirred at reflux for 24 hr, cooled to room temperature and evaporated in vacuo. The resulting oil was diluted with EtOH/H2O (90/30 mL) and potassium carbonate (4.2 g, 30.4 mmol) was added. The reaction mixture was stirred at reflux for 16 hr, evaporated in vacuo, diluted with water (150 mL) and acidified with 6N HCl to pH 3. The aqueous mixture was stirred at RT for 16 hr and the solid precipitates collected and dried under reduced pressure to provide a white sold product (5.95 g) 82%.

Workup

  1. temperatureat reflux for 24 hr
  2. customevaporated in vacuo
  3. additionwas added
  4. stirringThe reaction mixture was stirred
  5. temperatureat reflux for 16 hr
  6. customevaporated in vacuo
  7. additiondiluted with water (150 mL)
  8. stirringThe aqueous mixture was stirred at RT for 16 hr
  9. customthe solid precipitates
  10. customcollected
  11. customdried under reduced pressure
  12. customto provide

Sources & evidence

ORD record
ord-b63557d6c95c4cec8dd455a1041f3db0
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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