3-Phenylpyridine → 2-Methyl-5-phenylpyridine

HRID 2185019Notes

Reaction equation

HRID 2185019 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][Li]>O1CCCC1.CCOCC>[CH3:13][C:10]1[CH:11]=[CH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][N:9]=1

Participants

5

Reactant 2

HCID 138863-PhenylpyridineHCID 178418348HCID 178418348, compound

Product 1

HCID 767442-Methyl-5-phenylpyridineYield 21.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(phenyl)pyridine (1.55 g, 10 mmol) in tetrahydrofuran (10 ml) was stirred at −78° C. and treated with methyllithium (1.4 M, 7.5 mL, 10 mmol) in ether. The resulting yellow solution was stirred for 1 h, allowed to warm to 0° C., stirred 1 h, quenched with saturated ammonium chloride, and extracted with ether. The combined organic phase was washed with water and with brine, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed (silica gel, 25% ethyl acetate/hexane) to give the title compound (0.36 g).

Workup

  1. stirringstirred 1 h
  2. customquenched with saturated ammonium chloride
  3. extractionextracted with ether
  4. washThe combined organic phase was washed with water and with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1a33151a3f0943f6bfd16d9dc17ce728
Source dataset
uspto-grants-2002_06
Patent number
US06399656B1

Reaction notes

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