反应详情

A mixture of 4-(tert-butyldimethylsilyloxy)benzyloxyamine (3.10 g), ethyl 8-oxo-8-phenyloctanoate (6.32 g), acetic acid (2.07 ml), sodium acetate (1.98 g) and ethanol (80 ml) was heated under reflux for 20 hours. The reaction mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (60 ml), tetrabutylammonium fluoride trihydrate (3.98 g) was added and stirred at room temperature for 1 hour. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl E-8-(4-hydroxybenzyloxyimino)-8-phenyloctanoate (3.55 g, yield 77%) as a colorless oil from an ethyl acetate-hexane (2:7, v/v)-eluted fraction.

1. temperaturewas heated
2. temperatureunder reflux for 20 hours
3. extractionextracted with ethyl acetate
4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in tetrahydrofuran (60 ml)
8. additiontetrabutylammonium fluoride trihydrate (3.98 g) was added
9. additionWater was added to the reaction mixture
10. extractionextracted with ethyl acetate
11. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
12. dry with materialdried (MgSO4)
13. concentrationconcentrated