反应详情

温度

0 °C

In a dry round bottom flask under a blanket of nitrogen 60% sodium hydride in mineral oil (1.05 g, 26 mmol) was washed with hexanes and then suspended in N,N-dimethylformamide (50 mL). Mixture was cooled to 0° C. A solution of methyl 2-(methylsulfonamido)benzoate (5.0 g, 22 mmol) in 10 mL N,N-dimethylformamide was added to the mixture drop-wise. Reaction was held at 0° C. with stirring for 25 minutes. 2-(Trimethylsilyl)ethoxymethyl chloride was added to the mixture drop-wise. Reaction stirred for 2 hours slowly warming to ambient temperature. Reaction was quenched with 1N hydrochloric acid. Material was extracted twice with ethyl acetate. Material was washed successively with water and brine. Organic phase was dried (magnesium sulfate), filtered and concentrated to dryness. Residue was dissolved in N,N-dimethylformamide (5 mL) and added drop-wise to a mixture of 60% sodium hydride in mineral oil (1.02 g, 26 mmol) that had been washed with hexanes, suspended in N,N-dimethylformamide (50 mL) and cooled to 0° C. Ice bath was removed and the mixture was allowed to warm to room temperature. Reaction was held at room temperature overnight with stirring. Reaction was quenched with 1N hydrochloric acid. Material was extracted twice with ethyl acetate. Organic phase was washed successively with water and brine. Organic phase was dried (magnesium sulfate), filtered and concentrated to dryness. Silica gel chromatography (ethyl acetate-hexanes) afforded the title compound as a white solid in 72% yield. MS m/e (M−H)−=326.0.

1. customReaction
2. customwas held at 0° C.
3. customReaction
4. stirringstirred for 2 hours
5. temperatureslowly warming to ambient temperature
6. customReaction
7. customwas quenched with 1N hydrochloric acid
8. extractionMaterial was extracted twice with ethyl acetate
9. washMaterial was washed successively with water and brine
10. dry with materialOrganic phase was dried (magnesium sulfate)
11. filtrationfiltered
12. concentrationconcentrated to dryness
13. dissolutionResidue was dissolved in N,N-dimethylformamide (5 mL)
14. additionadded drop-wise
15. washhad been washed with hexanes
16. temperaturecooled to 0° C
17. customIce bath was removed
18. temperatureto warm to room temperature
19. customReaction
20. waitwas held at room temperature overnight
21. stirringwith stirring
22. customReaction
23. customwas quenched with 1N hydrochloric acid
24. extractionMaterial was extracted twice with ethyl acetate
25. washOrganic phase was washed successively with water and brine
26. dry with materialOrganic phase was dried (magnesium sulfate)
27. filtrationfiltered
28. concentrationconcentrated to dryness