HCID 53753365, compound → HCID 22323303, compound

HRID 496826Notes

Reaction equation

HRID 496826 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4](=[O:6])[CH3:5])#[N:2].[H][H]>CO.[Pd]>[OH2:6].[C:1]([CH:3]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:4](=[O:6])[CH3:5])#[N:2]

Participants

5

Reactant 2

HCID 53753365HCID 53753365, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22323303HCID 22323303, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of 3-cyano-4-phenyl-3-buten-2-one, prepared according to the procedure of Example 9 (5.0 g, 29.24 mmol), was dissolved in methanol (100 mL) containing 10% Pd—C (ca. 0.1 g, Aldrich) and hydrogenated at 50 psi hydrogen pressure for 2 h. The mixture was filtered through Celite to remove catalyst and an analytical sample prepared by concentrating a portion of the filtrate to give a pale-yellow oil. The oil was passed through a short pad of silica gel (hexane—ethyl acetate 7:3) and the desired fractions evaporated to give the title compound as a straw-colored oil. The remaining material was used directly in the next step.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove catalyst
  3. customan analytical sample prepared
  4. concentrationby concentrating a portion of the filtrate
  5. customto give a pale-yellow oil
  6. customthe desired fractions evaporated

Sources & evidence

ORD record
ord-6a18e0803c484d86ac3fb1ac93e87845
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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