Ethanol → HCID 72475368, compound

Participants

Reaction Conditions

Reaction Steps

In a sealed tube, a mixture of 40 mg (0.09 mmol) of 3-chloro-4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]benzaldehyde and 9 mg (0.135 mmol) hydroxylamine hydrochloride in 1 mL of ethanol and 1 mL glacial acetic acid was heated to 70° C. After 2 days, the reaction was concentrated under a stream of nitrogen. The residue was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from hexanes and then chromatographed on silica gel eluting with hexanes-ethyl acetate (9:1) to provide 18 mg (45%) of the title compound as an oil that crystallized upon standing, m.p. 136° C.-138° C.

Provenance & Evidence