反应详情

温度

-70 °C

To a solution of lithium bis(trimethylsilyl)amide (4.6 mL, 4.6 mmol, 1M in THF) in anhydrous 40 mL THF at −70° C. was slowly added over 15 minutes ((R)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one (685 mg, 3.8 mmol) as a solution in 4 mL THF. After the reaction mixture was stirred for 30 min at −70° C. a pre-cooled solution of (4-Iodo-but-2-enyloxymethyl)-benzene (1.3 g, 4.6 mmol) in 4 mL of THF was slowly added. The resulting mixture was stirred at −70° C. for 1 h and the temperature was slowly raised to room temperature over a period of 2 h. The mixture was poured into 20 mL saturated NH4Cl and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (2×30 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 827 mg of the title compound as a light yellow oil.

1. additionwas slowly added
2. temperaturethe temperature was slowly raised to room temperature over a period of 2 h
3. extractionextracted with ethyl acetate (3×50 mL)
4. washThe combined organic layers were washed with brine (2×30 mL)
5. dry with materialdried over Na2SO4
6. customThe solvent was removed under reduced pressure
7. customthe product isolated by Flash column chromatography
8. washeluting with 0% to 50% ethyl acetate/hexane