Propargyl bromide → HCID 85969570, compound

Participants

Reaction Steps

0.65 g (50% in mineral oil, 13.5 mmol) NaH are batchwise added to a solution, cooled to 0° C., of 2.0 g (13.5 mmol) 1H-indole-5-carbaldehyde in 80 mL THF and after heating to RT stirred for 15 min. Then a solution of 1.6 mL (80% in toluene, 15 mmol) propargyl bromide in 20 mL THF is slowly added dropwise and the reaction mixture is stirred overnight at RT. The mixture is evaporated down i. vac., the residue is combined with water, the aqueous phase is exhaustively extracted with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, gradient: cyc/EtOAc 4:1 to 2:1).

Provenance & Evidence