反应详情

To a suspension of sodium hydride (60% dispersion in mineral oil) (7.3 g, 0.183 mole) in anhydrous DMF (100 ml) under nitrogen atmosphere was added drop-wise 4-(4-hydroxyphenyl)-2-butanone 2 (20.0 g, 0.122 mole) in anhydrous DMF (100 ml) and the mixture was then stirred at room temperature for one hour. To this mixture was added drop-wise ethyl 4-bromobutyrate (28.5 g, 0.146 mole) in anhydrous DMF (50 ml), and the mixture was then stirred at 60° C. overnight. The DMF was removed under reduced pressure and water (200 ml) was then added to the residue and extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with brine (1×200 ml), dried over magnesium sulfate, filtered and evaporated to dryness. The residue obtained was purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluant to give 3 as a colourless oil (16.95 g, 50%).

1. stirringthe mixture was then stirred at 60° C. overnight
2. customThe DMF was removed under reduced pressure and water (200 ml)
3. additionwas then added to the residue
4. extractionextracted with ethyl acetate (3×200 ml)
5. washThe combined organic phases were washed with brine (1×200 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. customThe residue obtained
10. customwas purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluant