反应详情

To a solution of Dess-Martin periodinane (542 mg, 1.28 mmol) in THF (2 mL) was added methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (200 mg, 1.18 mmol) at 0° C., and the reaction mixture was then stirred at 20° C. for 3 hours before the addition of saturated aqueous sodium thiosulfate solution (50 mL). The mixture was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give methyl trans-4-formylcyclohexanecarboxylate. MS ESI calc'd. for C9H15O3[M+H]+ 171. found 171. 1H NMR: (400 MHz, CDCl3) δ 9.63 (s, 1H), 3.68 (s, 3H), 2.36-2.17 (m, 2H), 2.13-2.04 (m, 4H), 1.55-1.45 (m, 2H), 1.37-1.25 (m, 2H).

1. extractionThe mixture was extracted with ethyl acetate
2. dry with materialthe combined organic layers were dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by prep-TLC (ethyl acetate/petroleum ether)