Clopyralid → (3,6-Dichloropyridin-2-yl)methanol

Participants

Reaction Steps

BOP (1.27 g, 2.9 mmol) was added to a THF (10 mL) solution containing 3,6-dichloropyridine-2-carboxylic acid (0.5 g, 2.6 mmol) and DIEA (0.55 mL, 3.2 mmol). After 5 minutes sodium borohydride (103 mg, 2.7 mmol) was added and the solution stirred at room temperature for 20 minutes. The solution was partitioned between ethyl ether and aqueous 1N HCl. The organic phase was washed with water, brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. LCMS2 1.32 min. (M+H)=178

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