Acetone → 4-(6-Bromopyridin-2-yl)-2-methylbut-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (0.6 mL of 1.6M in hexanes, 0.96 mmol) was added to a cooled (−78° C.) solution of 2-bromo-6-ethynylpyridine (150 mg, 0.82 mmol) in tetrahydrofuran (4.1 mL). A tan slurry formed. The mixture was stirred for 30 minutes while warming to −30° C. at which time acetone (0.3 mL, 4.1 mmol) was added. The slurry dissolved to form a light orange solution. The reaction was stirred for an additional 2 hours while warming to 0° C. The reaction was quenched via the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered, concentrated in vacuo and purified via flash chromatography (0-50% ethyl acetate/hexanes) to afford the title compound as a white solid.

Provenance & Evidence