Methyl iodide → HCID 18799939, compound

Participants

Reaction Steps

A solution of 2-chloro-3-hydroxy-4-vinyl-6-(1-hydroxyethyl)-pyridine (1.46 g, 7.31 mmol) in 12 mL of N,N-dimethylformamide is treated with sodium hydride (292 mg, 60% in oil, 7.31 mmol) and stirred at room temperature for 1 h. The mixture is treated with methyl iodide (0.5 mL, 8.04 mmol) and stirred for 2 h. The reaction is diluted with 125 mL of ethyl acetate and washed with 4×50 mL of saturated sodium chloride. The organics are dried over potassium carbonate and concentrated in vacuo. The crude material is chromatographed over 150 g of silica gel (230-400 mesh), eluting with 25% ethyl acetate/hexanes to give 1.09 g (78%) of 2-chloro-3-methoxy-4-vinyl-6-(1-hydroxyethyl)-pyridine.

Provenance & Evidence