Chlorotrimethylsilane → Methyl 2-(2-methylquinolin-8-yl)acetate
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl[Si](C)(C)[CH3:18]>CO>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH2:12][C:13]([O:15][CH3:18])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-(2-methylquinolin-8-yl)acetic acid (1.45 g, 7.21 mmol) in dry MeOH (100 mL) was added chlorotrimethylsilane (1.82 mL, 14.4 mmol) dropwise at 0° C. After addition, the reaction mixture was stirred at reflux for 2 hours. After cooling to ambient temperature, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (20 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give methyl 2-(2-methylquinolin-8-yl)acetate (1.35 g, 87.0%) as an oil.