4-Toluenesulfonyl chloride → HCID 58216658, compound

Participants

Reaction Steps

2-[6-Chloro-2-(hydroxymethyl)pyridin-3-yl]propan-2-ol (200 mg, 0.99 mmol) was taken up in tetrahydrofuran (5 mL) and cooled to −78° C. n-Butyllithium (1.24 mL 011.6 M in hexanes, 1.98 mmol) was added dropwise and the mixture was allowed to stir for 30 minutes. p-Toluenesulfonylchloride (190 mg, 0.99 mmol) was then added in one portion and the mixture was allowed to warm to room temperature warm slowly to 0° C. over two hours and then left to warm to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride and the biphasic mixture was extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-50% ethyl acetate/hexanes) to afford the title compound as a colorless oil.

Provenance & Evidence