Water → Ethyl 1-(3-formylphenyl)cyclopropanecarboxylate

Participants

Reaction Steps

Ethyl 1-(3-bromophenyl)cyclopropanecarboxylate (538 mg, 1.9 mmol) was dissolved in acetone (20 mL). Osmium tetroxide (17.1 μL, 0.07 mmol) and NaIO4 (1.1 g, 5.6 mmol) were added followed by water (10 mL). The reaction mixture was stirred at room temperature for 18 h. Water was added (10 mL) followed by pentane (35 mL). The layers were separated and the aqueous layer was extracted with pentane (20 mL×2) and ethyl acetate (20 mL×2). The combined organics were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash chromatography (pentane/ethyl acetate 95:5) to afford the title compound as an oil (327 mg, 80%). MS (ES+) (M+H) 219.

Provenance & Evidence