反应详情

温度

60 °C

A mixture of 4-(4-hydroxyphenyl)-3-methyl-4-oxo-butyric acid ethyl ester (12.5 g, 52.9 mmol), 1-bromo-3-chloropropane (11.3 mL, 114.6 mmol) and K2CO3 (21.9 g, 159 mmol) in acetone (200 mL) was stirred at 60° C. for 15 h. The reaction was cooled to RT and filtered over celite and the filtrate was evaporated at reduced pressure to give a crude residue. The crude residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution and the aqueous layer was extracted twice with methylene chloride. The combined organics was washed with brine, dried (Na2SO4), filtered, and concentrated to provide a crude product. The crude product was purified by ISCO (330 g) chromatography using 15% EtOAc in hexane to produce 4-[4-(3-chloropropoxy)-phenyl]-3-methyl-4-oxo-butyric acid ethyl ester (9.7 g, 56%), MS m/z 267 (M−45)

1. temperatureThe reaction was cooled to RT
2. filtrationfiltered over celite
3. customthe filtrate was evaporated at reduced pressure
4. customto give a crude residue
5. customThe crude residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
6. extractionthe aqueous layer was extracted twice with methylene chloride
7. washThe combined organics was washed with brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customto provide a crude product
12. customThe crude product was purified by ISCO (330 g) chromatography