Propargyl bromide → HCID 14812561, compound

Participants

Reaction Steps

To a solution of 102 (10.0 g, 87.7 mmol) in acetonitrile (100 mL) was added K2CO3 (12.7 g, 92 mmol), LiI (0.59 g, 4.4 mmol) and propargyl bromide (11.0 g, 92 mmol). The resulting reaction mixture was refluxed for 24 h. Progress of the reaction was monitored using TLC. Upon completion of the starting material, the crude reaction mixture was filtered in a small pad of Celite and the solvent was evaporated under vacuum at room temperature. The crude material was passed through column eluting with EtOAc/hexane (3:7) to afford 103 (5.9 g) in 45% yield as a crystalline, pale yellow solid. 1H NMR (CDCl3) δ 7.45 (bs, 1H), 3.53 (d, J=2.2 Hz, 2H), 2.46 (s, 2H), 2.29 (t, J=2.6 Hz, 1H), 1.35 (s, 6H).

Provenance & Evidence