Hydrochloric Acid → 4-[2-(2,3-Dimethoxyphenyl)-1-hydroxyethyl]pyridine Hydrochloride

Participants

Reaction Steps

To a stirred solution of 2-(2,3-dimethoxyphenyl)-1-(4-pyridinyl)ethanone (2.4 g, 0.009 mol) in EtOH (25 ml) was added, portionwise, NaBH4 (0.005 mol). The reaction was stirred at ambient temperature for 2 h, and then it was poured into water. The aqueous solution was extracted with EtOAc, and the extract was washed (water), dried (magnesium sulfate) and concentrated to afford an oil. The oil was triturated with Et2O and 1.9 g of a white solid resulted. The solid was dissolved in EtOH and ethereal HCl was added to precipitate a white hydrochloride salt. The salt was recrystallized twice from EtOH to afford the alcohol as a white solid mp 204-206° C.

Provenance & Evidence