反应详情

A mixture of 1.7 g (17 mmol) of 2,4-pentanedione, 30 ml of benzene and 0.26 g (11.3 mmol) of sodium was warmed at reflux for 3 hours. The reaction mixture was cooled to room temperature and a solution of 10 mmol of 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanoyl chloride was added dropwise. The resulting mixture was warmed at reflux for 2.5 hours, stirred at room temperature overnight and poured into water and ether. The organic layer was separated, dried over MgSO4 and evaporated to dryness. The residue was purified by prep LC, eluting with 4:1 hexane:acetone. The product was taken up in ether and extracted with two portions of 1% aqueous NaOH. The combined aqueous layers were made acidic with aqueous HCl and extracted with ether. The ether layer was evaporated to dryness and the residue again purified by prep LC, eluting with 85:15 hexane:acetone. This gave a yellow oil which was thoroughly dried to leave 0.70 g product. Calc for C20H18BrFO5 : C, 54.93, H, 4.15. Found: C, 54.13, H, 4.30.

1. temperaturewas warmed
2. temperatureat reflux for 3 hours
3. temperatureThe resulting mixture was warmed
4. temperatureat reflux for 2.5 hours
5. customThe organic layer was separated
6. dry with materialdried over MgSO4
7. customevaporated to dryness
8. customThe residue was purified by prep LC
9. washeluting with 4:1 hexane
10. extractionextracted with two portions of 1% aqueous NaOH
11. extractionextracted with ether
12. customThe ether layer was evaporated to dryness
13. customthe residue again purified by prep LC
14. washeluting with 85:15 hexane
15. customThis gave a yellow oil which
16. customwas thoroughly dried