Nitric Acid → HCID 58959917, compound

Participants

Reaction Steps

To a solution of 42 mg (0.087 mmol) of 2-(3-chloro-2-fluoro-5-trifluoromethylbenzyl)-4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol in 2 mL of acetic acid was added a mixture of 15 μL of fuming nitric acid (90%) and 22 μL of sulfuric acid in 250 μL of acetic acid in several portions. The mixture eventually turned from clear to green to deep blue. After 5 minutes, the reaction was cautiously made basic with saturated aqueous sodium bicarbonate and extracted with four 6 mL portions of EtOAc. The combined organic layers were washed with three 5 mL portions of saturated aqueous sodium bicarbonate, two 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The yellow residue was purified by preparative chromatography (silica gel, EtOAc-hexanes, (2:8)) to afford 34 mg of partially purified product, a second preparative chromatography (silica gel, toluene-hexanes (6:4)) afforded 24 mg of the title compound.

Provenance & Evidence