反应详情

169 mg (0.5 mmole) of 4-octyl-5-(6-carboxyhexylidene)-3-hydroxycyclopentanone was dissolved in 3 ml of tetrahydrofuran, and ml of 0.5N hydrochloric acid was added. The mixture was stirred at room temperature for 4 days. A saturated aqueous solution of sodium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dried product was filtered, concentrated, and purified by preparative silica gel-thin-layer chromatography to give 12 mg (0.35 mmole; yield 70%) of 4-octyl-5-(6-carboxyhexylidene)-2-cyclopentanone. The resulting compound had the following spectral data.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationThe dried product was filtered
5. concentrationconcentrated
6. custompurified by preparative silica gel-thin-layer chromatography