Perchloric Acid → HCID 70818559, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyl 2-(4-bromo-5-chloro-2-methylthiophen-3-yl)-2-hydroxyacetate (44c) (334 mg, 1.065 mmol) in tert-butylacetate (10.9 mL) at −5° C. was added perchloric acid (70%, 0.4 mL). The mixture was stirred at −5° C. for 1 hour then at 0° C. for 30 minutes more. The mixture was stirred at room temperature for 1 hour more and was basified with a saturated aqueous solution of sodium bicarbonate until pH 8. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5) to afford the desired product (44d) as a colorless oil (324 mg, 0.88 mmol, 82%).

Provenance & Evidence