Hydrochloric Acid → 2-Ethynylquinoline

Participants

Reaction Steps

2-((Trimethylsilyl)ethynyl)quinoline (1.289 g, 5.72 mmol), and K2CO3 (0.792 g, 5.73 mmol) were dissolved in a mixture of methanol (3 mL) and dichloromethane (1.5 mL), followed by stirring at room temperature. The completion of the reaction was confirmed by TLC (EtOAc/Hexane=1:4). When the reaction was completed, the pH of the reactant was adjusted to 10 by addition of an aqueous solution of 1 M HCl and extracted with dichloromethane, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The thus obtained filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/Hexane=1:4, R.f: 0.3), to thereby obtain 2-ethynylquinoline (0.742 g, 85%) as brown oil.

Provenance & Evidence