3-Hydroxypyridine → HCID 19082034, compound

Participants

Reaction Steps

To a suspension of sodium hydride (70 mg, 2.8 mmol) and 3-hydroxypyridine (0.24 g, 2.56 mmol) in DMF was added dropwise 1 g (1 g, 2.8 mmol) of 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxypropyl iodide in DMF, and the mixture was stirred at room temperature for 2 days. The mixture was washed with water, extracted with ethyl acetate, and the organic layer was washed with water and dried over magnesium sulfate. The dry organic layer was concentrated in vacuo, passed through a pad of silica gel eluting with hexane/ethyl acetate (1:1) to afford 0.48 g (55.1%) of 3-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-pyridine, as an oil, which crystallized on standing in ether, m.p. 46°-49° C.

Provenance & Evidence