Iodine → 1-Quinoxalin-2-yl-but-3-yn-1-ol

Participants

Reaction Steps

To a mixture of magnesium (229 mg, 9.41 mmol), mercuric chloride (13 mg, 47 mmol) and few crystals of iodine in Et2O (1.5 mL), a solution of propargyl bromide (0.53 mL, 5.88 mmol) in Et2O (4.5 mL) was added slowly in order to maintain a reflux. The reaction mixture was stirred 1 hour and added to a solution of quinoxaline-2-carbaldehyde (500 mg, 3.16 mmol) in THF (2 mL). The resulting reaction mixture was stirred at 0° C. for 30 min., at room temperature for 30 min. and was poured onto saturated NH4Cl solution. The aqueous phase was extracted with Et2O. The aqueous phase was washed with water, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by C18 flash chromatography (H2O/acetonitrile 100:0 to 80:20) to yield 90 mg (0.45 mmol, 14%) of 1-quinoxalin-2-yl-but-3-yn-1-ol as a yellow oil.

Provenance & Evidence