反应详情

温度

80 °C

A solution of (rac)-(1S,8aR)-8a-butyl-6-(methoxymethoxy)-1-propyl-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (92 mg, 0.28 mmol) in methanol (1 mL) was treated with aqueous 2N HCl (0.42 mL, 0.84 mmol). The resulting mixture was stirred and gradually heated to 80° C. over 30 minutes, and then kept at 80° C. for an additional 30 minutes. After cooling, the mixture was diluted with EtOAc and washed with 5% NaHCO3. The aqueous portion was back-extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column, eluting with 5:1 hexane-EtOAc, to give (rac)-(1S,8aR)-8a-butyl-6-hydroxy-1-propyl-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as a white solid.

1. temperatureAfter cooling
2. washwashed with 5% NaHCO3
3. extractionThe aqueous portion was back-extracted with EtOAc
4. washThe combined organics were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column
9. washeluting with 5:1 hexane-EtOAc