(Diethylamino)sulfur trifluoride → HCID 68644248, compound

Participants

Reaction Steps

To a solution of 4-(5-(4-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethoxy)-benzonitrile (14) (600 mg, 1.6 mmol) in dry dichloromethane (20 mL) was slowly added DAST (251 mg, 1.6 mmol, in 50 mL dry dichloromethane) at −78° C. under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred for 3 hours. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using ethyl acetate:hexane:methyl alcohol (7:7:1) as an eluant to give 4-[4-fluoromethyl-6-methyl-5-(4-cyano-benzyloxy)-pyridin-3-ylmethoxy]-benzonitrile (18) (314 mg, 52% yield) as a colorless solid.

Provenance & Evidence