反应详情

Two hundred milligrams (0.78 mmol) of 3-acetoxy-5-t-butyldimethylsiloxycyclopent-1-ene was dissolved in 1.0 milliliter of a methanol solution of 1 normal barium hydroxide, after which the resulting solution was heated under reflux for 15 minutes in an atmosphere of nitrogen. The methanol was then distilled off under reduced pressure, after which ethanol was added to precipitate a solid, which was filtered off. Ehtanol was then distilled off from the filtrate, after which the concentrated residue was extracted with ether after addition of water thereto. The resulting organic layer was then thoroughly washed in water, dried with anhydrous sodium sulfate and thereafter concentrated to obtain a crude product. The so obtained product was then separated by preparative thin-layer chromatography (silica gel 2mm, hexane:ethyl acetate = 4:1) to obtain 75 milligrams (0.35 mmol, 45%) of 3-t-butyldimethylsiloxy-5-hydroxycyclopent-1-ene.

1. temperatureafter which the resulting solution was heated
2. temperatureunder reflux for 15 minutes in an atmosphere of nitrogen
3. distillationThe methanol was then distilled off under reduced pressure
4. additionafter which ethanol was added
5. customto precipitate a solid, which
6. filtrationwas filtered off
7. distillationEhtanol was then distilled off from the filtrate
8. extractionafter which the concentrated residue was extracted with ether
9. additionafter addition of water
10. washThe resulting organic layer was then thoroughly washed in water
11. dry with materialdried with anhydrous sodium sulfate
12. concentrationconcentrated
13. customto obtain a crude product
14. customThe so obtained product
15. customwas then separated by preparative thin-layer chromatography (silica gel 2mm, hexane:ethyl acetate = 4:1)