Sodium hydride → 2-Chloro-3-(2-methyl-1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine

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Reaction Steps

A solution of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine (4.49 g, 15 mmol) in 25 mL of N,N-dimethylformamide at 0° C. is treated with 600 mg (60% in oil, 15 mmol) of sodium hydride and stirred at room temperature for 1 h. The reaction is treated with 1.7 mL (16.5 mmol) of 2-methyl-3-bromopropene and stirred for 2 h. The mixture is diluted with 150 mL of ethyl acetate and washed with 4×50 mL of 1:1 50% saturated sodium chloride/sodium bicarbonate, and dried over potassium carbonate. The crude material is chromatographed over 150 g of silica gel (230-400 mesh), eluting with 25% ethyl acetate/hexanes to give 3.94 g (74%) of 2-chloro-3-(2-methyl-1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine.

Provenance & Evidence