反应详情

Carefully add NaH (10.83 g, 60% in oil, 270.8 mmol, 4 eq.) to EtOH (200 mL). When cool, add a solution of 5-trifluoromethyl-2-trimethylsilanylethynylphenylamine (22.3 g, 67.7 mmol) in EtOH (400 mL) with vigorous stirring. After 2 hours, heat to reflux. After 4 hours, evaporate in vacuo to remove the EtOH and dilute the residue obtained with water and extract with Et2O. Combine the organic layers and wash with brine, dry over MgSO4, filter, and evaporate to give a dark oil. Absorbed the oil onto silica gel and load onto short column of silica gel. Elute with 20% EtOAc in hexanes. Pool fractions containing the product and remove the solvent leaving a dark brown oil. Further purification of the oil by HPLC (silica column) using a gradient 1% Et2O in hexanes to 15% Et2O in hexanes. Pool fractions containing the product and remove the solvent to give the title compound as an orange solid: 1H NMR (300 MHz, d6-DMSO-d6): 6.58 (m, 1H), 7.28 (m, 1H), 7.61 (t, 1H), 7.74 (m, 2H), 11.51 (bs, 1H); MS(EI+): m/z 185 (M+).

1. temperatureWhen cool
2. temperatureheat to reflux
3. waitAfter 4 hours
4. customevaporate in vacuo
5. customto remove the EtOH
6. additiondilute the residue
7. customobtained with water
8. extractionextract with Et2O
9. washwash with brine
10. dry with materialdry over MgSO4
11. filtrationfilter
12. customevaporate
13. customto give a dark oil
14. customAbsorbed the oil onto silica gel and load onto short column of silica gel
15. washElute with 20% EtOAc in hexanes
16. additionPool fractions containing the product
17. customremove the solvent
18. customleaving a dark brown oil
19. customFurther purification of the oil by HPLC (silica column)
20. additionPool fractions containing the product
21. customremove the solvent