反应详情

Another variation to prepare 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone was performed starting from 2-(3-fluorophenyl)-1-{4-(methylsulfonyl)phenyl}-ethanone as follows: To a stirred solution of 2-(3-fluorophenyl)-1-(4-methylsulfonylphenyl)-ethanone (1 g) in 10 ml of THF, was added 0.23 g of 95% sodium hydride at 0° C. The reaction solution was stirred for 1 hour at the same temperature. Then 0.64 g of a-bromo-isobutyric cyanide was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred for another 7 hours while being allowed to warm to room temperature. Then the reaction was quenched with 5 ml of water. The mixture was concentrated in vacuo, and was dissolved in 50 ml of water. The aqueous solution was extracted with ethylacetate (100 ml). The organic layer was washed with brine, concentrated in vacuo. Then the resulting residue was purified by column chromatography (hexane/ethylacetate) to afford 0.75 g of 2,2-dimethyl-4-(3-fluorophenyl)-5-{(methylsulfonyl)phenyl}-3(2H)-furanone.

1. stirringThe reaction mixture was stirred for another 7 hours
2. customThen the reaction was quenched with 5 ml of water
3. concentrationThe mixture was concentrated in vacuo
4. dissolutionwas dissolved in 50 ml of water
5. extractionThe aqueous solution was extracted with ethylacetate (100 ml)
6. washThe organic layer was washed with brine
7. concentrationconcentrated in vacuo
8. customThen the resulting residue was purified by column chromatography (hexane/ethylacetate)