Phosphorus oxide (P4O10) → HCID 18544233, compound

HRID 1268142Notes

Reaction equation

HRID 1268142 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[CH:7]=[CH:6]2.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][CH:7]=[C:6]2[N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 31268PyrrolidineHCID 15892758HCID 15892758, compound

Product 1

HCID 18544233HCID 18544233, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5,6-Dimethoxy-1-indenone (5.1 g, 26.53 mmol) was dissolved in 120 mL of toluene. To this solution 17.7 mL (212 mmol) of pyrrolidine was added followed by 0.5 g of P2O5. The reaction mixture was refluxed for about 20 hours in a flask equipped with a Dean-Stark adapter. The flask was cooled to room temperature and the solvent was evaporated in vacuum leaving a brown-red solid. This solid was extracted with 50 mL of ether and filtered. The ether was evaporated leaving a brown solid. This solid was extracted with 120 mL of hot hexane and filtered. The hexane was removed and solid was dissolved in a mixture of 30 mL of toluene and 60 mL of hexane and filtered. The red solution was cooled to −27° C. overnight. The resulting solid was recovered by decantation, washed with cold hexane and dried under reduced pressure to give 2.97 g of 1-(5,6-dimethoxy-1H-inden-3-yl)pyrrolidine. Yield was 46 percent.

Workup

  1. temperatureThe reaction mixture was refluxed for about 20 hours in a flask
  2. customequipped with a Dean-Stark adapter
  3. customthe solvent was evaporated in vacuum
  4. customleaving a brown-red solid
  5. extractionThis solid was extracted with 50 mL of ether
  6. filtrationfiltered
  7. customThe ether was evaporated
  8. customleaving a brown solid
  9. extractionThis solid was extracted with 120 mL of hot hexane
  10. filtrationfiltered
  11. customThe hexane was removed
  12. dissolutionsolid was dissolved in a mixture of 30 mL of toluene and 60 mL of hexane
  13. filtrationfiltered
  14. temperatureThe red solution was cooled to −27° C. overnight
  15. customThe resulting solid was recovered by decantation
  16. washwashed with cold hexane
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-b5d45f958ff34939a3774928241019a6
Source dataset
uspto-grants-2003_04
Patent number
US06555634B1

Reaction notes

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