2-Phenyl-5-(prop-1-en-2-yl)pyridine → 5-Isopropyl-2-phenylpyridine

HRID 713560Notes

Reaction equation

HRID 713560 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:15])=[CH2:14])=[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]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 866740462-Phenyl-5-(prop-1-en-2-yl)pyridine

Product 1

HCID 30206225-Isopropyl-2-phenylpyridineYield 54%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2-Phenyl-5-(prop-1-en-2-yl)pyridine (11 g, 56.3 mmol) was added to a hydrogenator bottle containing EtOH (150 mL). The reaction mixture was degassed by bubbling N2 for 10 min. Pd/C (0.60 g, 5.63 mmol) and Pt/C (0.55 g, 2.82 mmol) were added to the reaction mixture. The reaction mixture was placed on the Parr hydrogenator for 1.5 h. The reaction mixture was filtered on a tightly packed Celite® bed and washed with dichloromethane. The solvent was removed on rotoevaporator 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 6 g (54%) of 2-phenyl-5-isopropylpyridine (HPLC purity: 100%). The product was confirmed by GC/MS.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling N2 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 rotoevaporator and GC/MS
  6. customThe crude product was chromatographed on silica gel with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-f98fdeb152774d36ba76a02c9bcfc579
Source dataset
uspto-grants-2015_11
Patent number
US09184397B2

Reaction notes

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