反应详情

To a refluxing solution of zinc dust (0.15 g, 20 mesh, activated prior to use by washing with 2% of hydrochloric acid, water, 95% ethanol, acetone and anhydrous ether, then dried in vacuum for several hours) in 6 ml of dry benzene was slowly added a mixture of bromo ethyl acetate (0.082 ml, 0.74 mmol) and ethyl 4-[(5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-yl)azo]benzoate (Compound D10, 0.13 g, 0.371 mmol) in 6 ml of dry benzene. The resulting mixture was refluxed for 2 h then cooled to room temperature. The precipitate was filtered through celite and the filtrate was washed with cold 15% sulfuric acid. The organic phase was washed with saturated sodium bicarbonate, brine, dried over Na2SO4, filtered and concentrated to give a red oil. Purification by flash chromatography (silica gel, 30% ethyl acetate in hexane) afforded the title compound as a red oil.

1. washby washing with 2% of hydrochloric acid, water, 95% ethanol, acetone and anhydrous ether
2. dry with materialdried in vacuum for several hours) in 6 ml of dry benzene
3. additionwas slowly added
4. temperatureThe resulting mixture was refluxed for 2 h
5. filtrationThe precipitate was filtered through celite
6. washthe filtrate was washed with cold 15% sulfuric acid
7. washThe organic phase was washed with saturated sodium bicarbonate, brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a red oil
12. customPurification by flash chromatography (silica gel, 30% ethyl acetate in hexane)