Hydrochloric Acid → HCID 86599504, compound

Participants

Reaction Steps

To a solution of ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Step 1 (600 mg, 1.24 mmole) in THF (20. mL) was added 30% H2O2 (192uL, 1.86 mmole) and aqueous NaOH (500 uL-2.5 N, 1.25 mmole) at 0° C. and the mixture was allowed to warm to room temperature. After stirring for 3.5 hrs, the mixture was acidified with 1N HCl, brine (50 mL) was added and the mixture was extracted with EtOAc (200 mL). The extract was dried over MgSO4, filtered and concentrated in vacuo to give a yellow crystalline solid. The crude product was purified by silica chromatography (0%-25% EtOAc in hexanes) to give 422 mg (91% yield) of the product as an off-white solid: EIHRMS m/z 372.0421 (M+, C14H10F6O5, Calc'd 372.0432).

Provenance & Evidence