3-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-vinyl}-benzonitrile → 3-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ethyl}-benzonitrile

HRID 1717769Notes

Reaction equation

HRID 1717769 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])=[CH2:17])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]>O=[Pt]=O.C(OCC)(=O)C>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:16]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])[CH3:17])=[CH:14][CH:15]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 666996573-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-vinyl}-benzonitrile

Product 1

HCID 666995733-{1-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ethyl}-benzonitrile

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add 3-{1-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-vinyl}-benzonitrile (0.105 g, 0.255 mmol), ethyl acetate (50 ml) and PtO2 (0.010 g) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 KPa), seal the vessel and agitate the reaction at ambient temperature. Continue the reaction for 2.5 hours. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the platinum catalyst. Add the filtrate and PtO2 (0.019 g) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 KPa), seal the vessel and agitate the reaction at ambient temperature. Continue the reaction for 6 hours. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the platinum catalyst and remove the solvent under vacuum. Add the concentrate, ethyl acetate (50 ml) and PtO2 (0.022 g) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 KPa), seal the vessel and agitate the reaction at ambient temperature. Continue the reaction for 18 hours. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the platinum catalyst and remove the solvent under vacuum. Add the concentrate, ethyl acetate (150 ml), Pt catalyst from previous filtrations and PtO2 (0.105 g) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 KPa), seal the vessel and agitate the reaction at ambient temperature. Continue the reaction for 22.5 hours. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the platinum catalyst. The mixture is filtered and concentrated to give 25 mg, 25%, as a film. LCMS M−1 412.

Workup

  1. customPurge the reaction vessel with nitrogen
  2. customseal the vessel
  3. customthe reaction at ambient temperature
  4. customthe reaction for 2.5 hours
  5. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  6. filtrationFilter the reaction mixture
  7. customto remove the platinum catalyst
  8. additionAdd the filtrate and PtO2 (0.019 g) to a Parr pressure vessel
  9. customPurge the reaction vessel with nitrogen
  10. customseal the vessel
  11. stirringagitate
  12. customthe reaction at ambient temperature
  13. customthe reaction for 6 hours
  14. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  15. filtrationFilter the reaction mixture
  16. customto remove the platinum catalyst
  17. customremove the solvent under vacuum
  18. additionAdd the concentrate, ethyl acetate (50 ml) and PtO2 (0.022 g) to a Parr pressure vessel
  19. customPurge the reaction vessel with nitrogen
  20. customseal the vessel
  21. stirringagitate
  22. customthe reaction at ambient temperature
  23. customthe reaction for 18 hours
  24. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  25. filtrationFilter the reaction mixture
  26. customto remove the platinum catalyst
  27. customremove the solvent under vacuum
  28. additionAdd the concentrate, ethyl acetate (150 ml), Pt catalyst
  29. filtrationfrom previous filtrations and PtO2 (0.105 g) to a Parr pressure vessel
  30. customPurge the reaction vessel with nitrogen
  31. customseal the vessel
  32. stirringagitate
  33. customthe reaction at ambient temperature
  34. customthe reaction for 22.5 hours
  35. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  36. filtrationFilter the reaction mixture
  37. customto remove the platinum catalyst
  38. filtrationThe mixture is filtered
  39. concentrationconcentrated
  40. customto give 25 mg, 25%

Sources & evidence

ORD record
ord-105ee59f66f7499c9daab11d202b3639
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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