Hydrochloric Acid → HCID 23103646, compound

Participants

Reaction Conditions

Reaction Steps

A 1.58 M n-hexane solution of n-butyllithium (19.0 mL, 0.0300 mol) and THF (50 mL) were mixed, followed by addition of 2,2,6,6-tetramethylpiperidine (4.2 g, 0.0300 mol) at −78° C. The reaction mixture was warmed to 0° C. and stirred for 20 minutes. After the reaction mixture was cooled again to −78° C., a solution of 2-chloropyrazine (2.5 g, 0.0218 mol) in THF (5 mL) was added dropwise thereto and stirred at −78° C. for 1 hour. A solution of 4-ethylbenzaldehyde (3.3 g, 0.0240 mol) in THF (5 mL) was added dropwise to the reaction mixture, followed by stirring for 30 minutes. Concentrated hydrochloric acid (10 mL) and ethanol (5 mL) were added to the reaction mixture. After warming to room temperature, the reaction mixture was poured into saturated aqueous sodium bicarbonate and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give (2-chloropyrazin-3-yl)-(4-ethylphenyl)methanol (3.1 g, 57%) as a brown oil.

Provenance & Evidence