反应详情

温度

-78 °C

A 1M tetrahydrofuran solution (0.6 ml) of lithium bis-(trimethylsilyl)amide was added to 1 ml of tetrahydrofuran under an argon atmosphere, and the mixture was cooled to -78° C. To this solution were added, dropwise with stirring, a tetrahydrofuran solution (2 ml) of 125 mg of (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-4-oxo-pentylamine, followed by a tetrahydrofuran solution (2 ml) of 94 mg of 3-(3-thienyl)-benzaldehyde. The mixture was stirred at -78° C. for 1 hour, and then at 0° C. for 1 hour. The reaction mixture was neutralized with acetic acid, and ethyl acetate and water were added to extract it. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [ethyl acetate→ethyl acetate/methanol=20/1] to give 78 mg (yield 40%) of (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-6-hydroxy-4-oxo-6-[3-(3-thienyl)phenyl] hexenylamine.

1. additionTo this solution were added
2. stirringThe mixture was stirred at -78° C. for 1 hour
3. additionwere added
4. extractionto extract it
5. customThe organic layer was separated
6. washwashed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe desiccant was separated by filtration
9. customthe solvent was evaporated under reduced pressure
10. customThe residue was purified by silica gel column chromatography [ethyl acetate→ethyl acetate/methanol=20/1]