Hydrogen Peroxide → HCID 58042378, compound

Participants

Reaction Steps

To the crude 2-cyclopropyl-3-(1,1-difluoroethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 268, 412 mg, 1.27 mmol) was added methanol (20 mL), and the stirred solution cooled in an ice bath. To the solution was added hydrogen peroxide solution (35% in water) (0.15 mL, 1.52 mmol) over 2 minutes. The solution was allowed to warm slowly to room temperature over 18 hours. The reaction was quenched by addition of 1M aqueous sodium thiosulfate solution (50 mL), and rapidly stirred for 15 minutes. The organics were removed in vacuo, and brine (50 mL) was added. The aqueous was extracted into ethyl acetate (3×100 mL). The combined organics were dried over magnesium sulfate, filtered and the solvent removed to leave an orange oil. The oil was purified through a plug of silica, eluting with 1:1 ethyl acetate:heptane to provide the title compound a white solid (155 mg, 57%).

Provenance & Evidence