反应详情

To a dry schlenk flask was added 3-(4-((4-(bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propan-1-ol (1.16 g, 2.01 mmol) and 4-dimethylaminopyridine (0.012 g, 0.100 mmol. The flask was evacuated under vacuum and filled with nitrogen before addition of anhydrous tetrahydrofuran (2.0 mL). The mixture was placed in an ice bath and allowed to stir for 10 minutes. Triethylamine (0.712 g, 7.04 mmol) was added and the reaction was allowed to stir for 10 minutes. Added methanesulfonyl chloride (0.691 g, 6.03 mmol) and allowed mixture to stir for 5 minutes. The ice bath was removed and the mixture was stirred at room temperature while being monitored by thin layer chromatography (1:2 hexanes:ethyl acetate). Upon disappearance of the starting material the reaction mixture was poured into a separatory funnel containing 100 mL of cold water. The product was extracted using 3×50 mL ether. The organic layers were combined and washed with 3×50 mL of water, sodium bicarbonate solution, and sodium chloride solution. The resulting ether layers were dried over MgSO4. The drying agent was removed by filtration and the solvent was removed under reduced pressure. The residual solvent was removed in vacuo. The material was purified by flash chromatography (silica gel, 4:2 toluene:ethyl acetate) to yield an off-white solid (0.967 g, 73.3%). 1H NMR (400 MHz, C3D6O) δ 6.96 (m, 8H), 6.85 (m, 8H), 6.80 (s, 4H), 4.43 (t, J=6.3 Hz, 2H), 4.09 (t, J=6.0 Hz, 2H), 3.74 (s, 9H), 3.09 (s, 3H), 2.19 (q, J=6.2 Hz, 2H). 13C{1H} NMR (400 MHz, C3D6O) δ 156.42, 156.39, 155.30, 143.73, 143.49, 142.62, 142.26, 142.22, 126.33, 126.28, 126.00, 123.91, 123.69, 116.14, 115.41, 67.94, 64.61, 55.63, 36.97, 29.87. HRMS-EI (m/z): [M]− calcd for C37H38N2O7S, 654.24. found, 654.1). Anal. Calcd for C37H38N2O7S: C, 67.87; H, 5.85; N, 4.28. Found: C, 67.61; H, 5.77; N, 4.26.

1. customThe flask was evacuated under vacuum
2. additionfilled with nitrogen before addition of anhydrous tetrahydrofuran (2.0 mL)
3. customThe mixture was placed in an ice bath
4. stirringto stir for 10 minutes
5. stirringto stir for 5 minutes
6. customThe ice bath was removed
7. stirringthe mixture was stirred at room temperature
8. additionUpon disappearance of the starting material the reaction mixture was poured into a separatory funnel
9. additioncontaining 100 mL of cold water
10. extractionThe product was extracted
11. washwashed with 3×50 mL of water, sodium bicarbonate solution, and sodium chloride solution
12. dry with materialThe resulting ether layers were dried over MgSO4
13. customThe drying agent was removed by filtration
14. customthe solvent was removed under reduced pressure
15. customThe residual solvent was removed in vacuo
16. customThe material was purified by flash chromatography (silica gel, 4:2 toluene:ethyl acetate)