Water → (2,4-dichloro-6-methylpyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Ethyl 2,4-dichloro-6-methylnicotinate (9) (8.04 g, 34.3 mmol) was dissolved in THF (40 mL) and added to a stirred suspension of LAH (6.52 g, 0.170 mmol) in THF (80 mL) at −78° C. The mixture was stirred for 6 hours at this temperature and for 1 hour at −30° C. followed by cautious treatment with water (5.5 mL), 15% aqueous NaOH (5.5 mL) and water (16.5 mL) with vigorous stirring. The mixture was warmed to room temperature and filtered. The white precipitate was washed liberally with ethyl acetate. The combined organic portions were dried (MgSO4) and concentrated under vacuum to afford 6.40 g (97%) of (10) as a colorless oil which solidified on standing: LCMS (MH+, 192).

Provenance & Evidence