HCID 86674045, compound → HCID 58675901, compound

HRID 2369742Notes

Reaction equation

HRID 2369742 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([CH3:15])=[CH2:14])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].[Pt].CCO>[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 86674045HCID 86674045, compound

Product 1

HCID 58675901HCID 58675901, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2-Phenyl-4-(prop-1-en-2-yl)pyridine (13.5 g, 69.1 mmol) was added to a hydrogenator bottle containing EtOH (150 mL). The reaction mixture was degassed by bubbling with nitrogen for 10 min. Pd/C (0.736 g, 6.9 mmol) and Pt/C (0.674 g, 3.5 mmol) was added to the reaction mixture. The reaction mixture was placed on the Parr hydrogenator for 2 h. The reaction mixture was filtered on a tightly packed Celite® bed and washed with dichloromethane. The solvent was removed on a rotary evaporator and GC/MS confirmed complete conversion. The crude product was adsorbed on Celite® for column chromatography. The crude product was chromatographed on silica gel with 10% EtOAc in hexane to yield 10 g (75%) of 2-phenyl-4-isopropylpyridine (HPLC purity: 99.8%). The product was confirmed by GC/MS.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling with nitrogen for 10 min
  3. filtrationThe reaction mixture was filtered on a tightly packed Celite® bed
  4. washwashed with dichloromethane
  5. customThe solvent was removed on a rotary evaporator and GC/MS
  6. customThe crude product was chromatographed on silica gel with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-f062ca0e667a46d48c551ec0702d7aac
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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