反应 #64387

反应方程式

HCl

n-BuLi

4-ethylphenyl-t-butylsulfonamide

B(OiPr)3

→

titled compound

2-t-butylsulfonamido-5-ethylphenylboric acid

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONTo the mixture, containing the bright orange dianion at 0° C.
2. 2
   温度to warm to rt
3. 3
   workup.STIRRINGstirred overnight
4. 4
   workup.STIRRINGthe mixture was stirred for 1 h
5. 5
   其他The solvent was removed under reduced pressure
6. 6
   萃取the residue was extracted with EtOAc
7. 7
   洗涤The organic was washed with 2N HCl, H2O and brine
8. 8
   干燥The organic was dried over anhydrous MgSO4
9. 9
   浓缩concentrated in vacuo

实验过程

To a solution of 4-ethylphenyl-t-butylsulfonamide (6.44 g, 26.7 mmoL) in anhydrous THF (60 mL) cooled to -20° C. under N2 was added 2.5M n-BuLi solution (27 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright orange dianion at 0° C., was added B(OiPr)3 (9.3 mL, 1.5 equiv). The reaction was allowed to warm to rt and stirred overnight. The next day 2N HCl (3 mL) was added and the mixture was stirred for 1 h. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic was washed with 2N HCl, H2O and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. Rf=0.5 (1:1 EtOAc/Hex). The material was used in subsequent steps without further purification.

来源