Hydrochloric Acid → HCID 58959937, compound

Participants

Reaction Steps

To a solution of 24 mg (0.061 mmol) of 3-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]benzonitrile in EtOH was added 15 mg (0.23 mmol) of potassium hydroxide followed by 0.2 mL of 30% aqueous hydrogen peroxide. The mixture was stirred for 24 hours and then diluted with water, made acidic with 1 N aqueous HCl, and extracted with three 5 mL portions of EtOAc. The combined organic layers were washed with two 5 mL portions of saturated aqueous sodium bicarbonate, two 5 mL portion of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford crude product which was purified on silica gel using dichloromethane-hexanes (1:1) to load the sample and then eluting with EtOAc-hexanes (1:99, then 3:97, then 6:93, then 1:9, then 2:8, then 3:7, then 4:6, then 1:1) to afford 17 mg (67%) of the title compound as a clear resin, m.p. 70° C.-75° C.

Provenance & Evidence