反应详情

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.

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with pentane (20 mL×2) and ethyl acetate (20 mL×2)
3. washThe combined organics were washed with water
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified via flash chromatography (pentane/ethyl acetate 95:5)