反应详情

Into a flask were added 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione (128 mg, 0.5 mmol), Ru[(S,S)-Tsdpen](p-cymene) (15 mg, 0.025 mmol, 5 mol %), methylene chloride (5 mL) and formic acid-triethylamine mixture (5:2, 1.3 ml). The resulting suspension mixture was stirred at room temperature for 24 hours, and then diluted with water and 10% aqueous hydrochloric acid solution. The aqueous layer was extracted with chloroform twice, and the extract was washed with water and a saturated aqueous sodium chloride solution sequentially, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione (NQ801) (115 mg, 89%, 96% ee) as a yellow crystal.

1. extractionThe aqueous layer was extracted with chloroform twice
2. washthe extract was washed with water
3. customa saturated aqueous sodium chloride solution sequentially, and evaporated in vacuo
4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)