Water → 5-Chloro-2-methyl-3-pyridinemethanol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 950 mg (5.12 mmol) of methyl 5-chloro-2-methylnicotinate in 20 mL of THF at 0° C. was added 500 mg (13.2 mmol) of LiAlH4 in 2 portions. After stirring at 0° C. for about 1 h., the following were added in succession: 0.5 mL of H2O, 0.5 mL of 15% NaOH (aqueous), and 1.5 mL of brine. The ice bath was removed and stirring was continued for 2 h. The mixture was filtered through Celite and concentrated. Purification by flash silica gel chromatography (2% MeOH/CHCl3) provided 399 mg of (5-chloro-2-methylpyridin-3-yl)methanol as an orange-yellow oil in 50% yield.

Provenance & Evidence