Hydrochloric Acid → (4-Chloro-3,5-dimethylpyridin-2-YL)methanol

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Reaction Steps

4-Chloro-2-ethoxycarbonyl-3,5-Lutidine (1 equivalent) was dissolved in methanol (4 volumes). The solution was cooled in an ice bath and while stirring sodium borohydride (1-4 eq.) was added in portions. The mixture was stirred and heated to reflux (80-85ℑC.). At the end of the reaction, the solvent was evaporated, water (2 volumes) was added and the product was extracted with toluene (2×4 volumes). The combined organic layers were stirred in an ice bath and HCl gas (1.2 eq.) was bubbled in solution. The 4-Chloro-2-hydroxymethyl-3,5-Lutidine hydrochloride salt was filtered, washed with toluene and dried at 50ℑ C. at high vacuum. The product was obtained as a white solid in 85% yield.

Provenance & Evidence