反应详情

温度

-70 °C

To a stirred −70° C. suspension of 0.26 g (1 mmol) 2-isopropoxy-5-methanesulfonyl-benzoic acid (CAS: 845616-02-6) and 0.75 ml (5 mmol) TMEDA in 2.6 ml THF was added dropwise a LDA solution (prepared from a 1.3 ml (2.1 mmol) 1.6M n-butyllithium solution in hexane and 0.3 ml (2.1 mmol) diisopropylamine in 2.5 ml THF at 0° C.). The light yellow suspension was stirred at −70° C. for 30 minutes. A solution of 0.19 ml (1.3 mmol) (iodomethyl)trimethylsilane in 0.5 ml THF was added dropwise over a period of 5 minutes. The yellow suspension was stirred at −70° C. for 15 minutes and then allowed to warm to room temperature. The light yellow solution was stirred at room temperature for 1 hour and then quenched with 5 ml brine. The mixture was diluted with 5 ml water. The mixture was concentrated in vacuo. The aqueous layer was carefully acidified with HCl 1N and extracted 3 times with dichloromethane. The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.21 g (63%) of the title compound as a yellow oil. MS (m/e): 343.0 [M−H]+.

1. stirringThe yellow suspension was stirred at −70° C. for 15 minutes
2. temperatureto warm to room temperature
3. stirringThe light yellow solution was stirred at room temperature for 1 hour
4. customquenched with 5 ml brine
5. additionThe mixture was diluted with 5 ml water
6. concentrationThe mixture was concentrated in vacuo
7. extractionextracted 3 times with dichloromethane
8. dry with materialThe combined extracts were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude was purified with flash column chromatography on silica eluting with a gradient
12. customformed from heptane and ethylacetate