Triphenylphosphine → HCID 22110943, compound

HRID 565380Notes

Reaction equation

HRID 565380 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=O)[C:36]([F:39])([F:38])[F:37])=[CH:30][C:29]=1[I:41])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO[CH:44](OC)[CH2:45][NH2:46]>C(Cl)(Cl)(Cl)Cl>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:44]=[CH:45][N:46]=[C:35]2[C:36]([F:39])([F:38])[F:37])=[CH:30][C:29]=1[I:41])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 22618201HCID 22618201, compound

Product 1

HCID 22110943HCID 22110943, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Triphenylphosphine (3.11 g, 11.88 mmol) was added to a suspension of N-(4-benzyloxy-3-iodophenyl)trifluoroacetamide (Description 15; 2.5 g, 5.94 mmol) in carbon tetrachloride (35 ml) and the mixture was heated under reflux for 24 hours. The mixture was then allowed to cool and the solvent was evaporated under reduced pressure. Hexane was then added and the mixture was heated under reflux for 1 hour. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in THF (20 ml), aminoacetaldehyde dimethyl acetal (2.5 ml, 22.9 mmol) was added and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and acetic acid was added. The mixture was heated under reflux for 3 hours, cooled and diluted with water. The mixture was basified and extracted with ethyl acetate. The organic extract was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (75:25) to give the title compound as a pale yellow oil (900 mg, 34%). 1H NMR (360 MHz, CDCl3) δ 7.80 (1H, d, J 2.5 Hz), 7.50 (2H, m), 7.44−7.43 (3H, m), 7.30 (1H, dd, J 2.5, 8.7 Hz), 7.20 (1H, s), 7.10 (1H, s), 6.91 (1H, d, J 8.7 Hz), and 5.22 (2H, s). m/z (ES+) 445 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool
  4. customthe solvent was evaporated under reduced pressure
  5. additionHexane was then added
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 1 hour
  8. filtrationThe mixture was filtered
  9. customthe solvent was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in THF (20 ml)
  11. customThe solvent was evaporated under reduced pressure and acetic acid
  12. additionwas added
  13. temperatureThe mixture was heated
  14. temperatureunder reflux for 3 hours
  15. temperaturecooled
  16. additiondiluted with water
  17. extractionextracted with ethyl acetate
  18. extractionThe organic extract
  19. dry with materialwas dried (MgSO4)
  20. customthe solvent was evaporated under reduced pressure
  21. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (75:25)

Sources & evidence

ORD record
ord-8a4e20acc5ed44ca8f629102b15b8154
Source dataset
uspto-grants-2001_01
Patent number
US06172077B2

Reaction notes

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