反应详情

温度

-25 °C

In a 100 mL round bottom flask containing 119b (500 mg, 1.7 mmol) under nitrogen was added anh. THF (20 mL) and anh.toluene (5 mL) and the mixture stirred and cooled to −20 to −30° C. 3.0M methylmagnesium bromide in diethylether (1.6 mL, 4.75 mmol) was then slowly added. After the addition the reaction was allowed to slowly warm to room temp. and stir for about 3 hrs after which the reaction was quenched with 1N HCl. Concentrated to remove THF, diluted with ethyl acetate and water then adjusted the pH to ˜6-7 with 1M NaOH. Separated and extracted 2× with ethyl acetate washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography: ISCO 24 g silica, ethyl acetate/hexanes, to give 119c.

1. additionAfter the addition the reaction
2. temperatureto slowly warm to room temp.
3. customwas quenched with 1N HCl
4. concentrationConcentrated
5. customto remove THF
6. additiondiluted with ethyl acetate and water
7. customSeparated
8. extractionextracted 2× with ethyl acetate
9. washwashed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customThe residue was purified by chromatography