3-Phenylpyridine → 2-Methyl-5-phenylpyridine

HRID 1084426Notes

Reaction equation

HRID 1084426 reaction equation
[Li][CH3:2].[C:3]1([C:9]2[CH:10]=[CH:11][CH:12]=[N:13][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCOCC>[CH3:2][C:12]1[CH:11]=[CH:10][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 138863-PhenylpyridineHCID 178418348HCID 178418348, compound

Product 1

HCID 767442-Methyl-5-phenylpyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. solution of 1.4 M MeLi in Et2O (35 mm) was added 5-phenylpyridine (4.65 g). The Et2O was distilled off almost completely and replaced by THF (15 cc) and the solution was refluxed for 1 hour. 25% aqueous NH4OAc (25 cc) was added and the mixture extracted with ethyl acetate (2×50 cc). The organic layer was washed with brine and the solvents removed in vacuo. The residue was purified by chromatography to afford the title compound. p.m.r. (CD3COCD3) δ 8.7 (d, 1H), 7.2-7.9 (m, 7H), 2.5 (s, 3H).

Workup

  1. distillationThe Et2O was distilled off almost completely
  2. temperaturethe solution was refluxed for 1 hour
  3. addition25% aqueous NH4OAc (25 cc) was added
  4. extractionthe mixture extracted with ethyl acetate (2×50 cc)
  5. washThe organic layer was washed with brine
  6. customthe solvents removed in vacuo
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-9bc687ecf7084b2a8388b6b82becd69f
Source dataset
uspto-grants-1991_04
Patent number
US05004743

Reaction notes

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