Triphenylphosphine → 3-[3-[4-(5-Methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-quinoline

Participants

Reaction Steps

A mixture of 3-(3-hydroxypropyl)-quinoline (250 mg, 1.34 mmol), 4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol (273 mg, 1.34 mmol), and DEAD (256 mg, 1.47 mmol) was dissolved in 12 ml of THF. To the above solution was added triphenylphosphine (385 mg, 1.47 mmol) at 20° C. and the mixture was stirred overnight. The solvent was removed in vacuo, and the residue was partitioned between an aqueous sodium bicarbonate solution and methylene chloride. The aqueous layer was extracted with methylene chloride (3x), and the organic layer dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (20 cm column, ethyl acetate/hexane, from 1/5 to 1/3) to afford 364 mg (73%) of 3-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-quinoline, m.p. 105°-107° C.

Provenance & Evidence