反应详情

To a stirred solution of alcohol (65 mg, 0.14 mmol, Example 306) in acetone (4 mL), Jones reagent (made by adding 0.5 mL of concentrated sulfuric acid to a solution of chromium(VI) oxide, 0.67 g, Aldrich, in 2 mL of water) was slowly added until the orange color persisted for 20 minutes. The mixture was stirred for 1 hour and 2 mL of isopropanol was added. The mixture was again stirred for 30 minutes followed by slow addition of saturated sodium bicarbonate solution until pH=7. The mixture was extracted with ethyl acetate/tetrahydrofuran (2:1, 3×10 mL) and the extracts were combined and dried with sodium sulfate. The solvent was removed and the residue was chromatographed on HPLC (20–70%) to give a white solid, 4.3 mg, 7%. MS (ES) MH+=456.

1. stirringThe mixture was again stirred for 30 minutes
2. extractionThe mixture was extracted with ethyl acetate/tetrahydrofuran (2:1, 3×10 mL)
3. dry with materialdried with sodium sulfate
4. customThe solvent was removed
5. customthe residue was chromatographed on HPLC (20–70%)
6. customto give a white solid, 4.3 mg, 7%