3-Phenylpyridine → 2-Methyl-5-phenylpyridine

HRID 892221

Reaction equation

HRID 892221 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]>C(OCC)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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 cooled (−70° C.) solution of 3-phenylpyridine (1.43 mL, 10.0 mmoles) in diethyl ether (7.5 mL) is added dropwise methyllithium (LiBr complex, 1.5 M in diethyl ether, 7.33 mL, 11.0 mmoles). After letting warm to room temperature over 16 hours the reaction is cooled (0° C.) and quenched with distilled water (5 mL). The reaction is then extracted with methylene chloride, the organic layer isolated and concentrated, and the resulting residue purified by column chromatography (silica, 3:1 hexane: EtOAc) to yield the title compound as a pale yellow oil. MS(ESI) 170 (M+H)+.

Workup

  1. temperatureis cooled (0° C.)
  2. customquenched with distilled water (5 mL)
  3. extractionThe reaction is then extracted with methylene chloride
  4. customthe organic layer isolated
  5. concentrationconcentrated
  6. customthe resulting residue purified by column chromatography (silica, 3:1 hexane: EtOAc)

Sources & evidence

ORD record
ord-9f391ccfc2a144e1b9db62899f3d1216
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Linked notes

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