3-Phenylpyridine → 2-Methyl-5-phenylpyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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)+.