反应详情

Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionate (31 g) was dissolved in 465 ml of acetone, and 46 ml of Jones reagent prepared by adding 10.2 ml of conc. sulfuric acid and 12 g of chromic (VI) oxide to 45 ml of water was added dropwise with stirring under ice-cooling. After 3-hour-stirring at room temperature, an excess amount of Jones reagent was decomposed by adding isopropyl alcohol, The reaction mixture was poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=7.5:1) to provide 18.16 g of the objective compound as oil.

1. additionwas added dropwise
2. temperaturecooling
3. stirringAfter 3-hour-stirring at room temperature
4. additionThe reaction mixture was poured into ice-cold water
5. extractionextracted with ethyl acetate
6. washwashed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=7.5:1)