反应详情

温度

-78 °C

A flask charged with 0.23 mL (2.5 mmol) of dimethyl t-butoxycarbonyl-methylphosphonate in 8.75 mL of dry THF/DMPU (10:1). The flask was cooled to −78° C. where 1.78 mL (0.9 mmol, 2.5M hexanes) of n-butyl lithium was added slowly via syringe. The reaction mixture was stirred at −78° C. for 10 minutes and then a solution of 0.35 g (0.86 mmol) of Compound 14E in 3 mL of dry THF was added. After warming to room temperature and an additional 20 minutes of stirring, the reaction was quenched with 3 mL of water and then partitioned with 10 mL of saturated ammonium chloride and 20 mL of ethyl acetate, The water layer was further extracted with ethyl acetate (2×15 mL) and the combined organic layers were then washed with brine (10 mL), dried over magnesium sulfate, filtered and excess solvent was removed on the rotary evaporator. The crude product was purified by flash chromatography (3.5:1 EtOAc/Hexanes) to give 0.16 g (41%) of the product as a white solid. MS (electrospray): mass calculated for C23H22F3NO5, 449.15; m/z found 450, [M+H]+.

1. additionwas added slowly via syringe
2. temperatureAfter warming to room temperature and an additional 20 minutes
3. stirringof stirring
4. customthe reaction was quenched with 3 mL of water
5. custompartitioned with 10 mL of saturated ammonium chloride and 20 mL of ethyl acetate
6. extractionThe water layer was further extracted with ethyl acetate (2×15 mL)
7. washthe combined organic layers were then washed with brine (10 mL)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customexcess solvent was removed on the rotary evaporator
11. customThe crude product was purified by flash chromatography (3.5:1 EtOAc/Hexanes)