Potassium Carbonate → HCID 50998807, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[C:13][Si](C)(C)C)[CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)#[CH:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-methyl-6-trimethylsilanylethynyl-quinoline (2.1 g, 1.03 mmol, 1 eq) in solution in MeOH (5 mL) was added K2CO3 (5.69 g, 4.12 mmol, 4 eq), and the resulting mixture was stirred overnight at room temperature. The solvent was then removed under reduced pressure and water was then added. The aqueous layer was extracted twice with cyclohexane, and then the combined organic layers were washed with brine and dried over MgSO4. After filtration and concentration under reduced pressure the crude product was purified by column chromatography on silica gel (Cyclohexane-EtOAc 99:1) to afford 169 mg of 6-ethynyl-2-methyl-quinoline as a yellow crystal (98%).