反応 #64387

反応方程式

HCl

n-BuLi

4-ethylphenyl-t-butylsulfonamide

B(OiPr)3

→

titled compound

2-t-butylsulfonamido-5-ethylphenylboric acid

溶媒

THF

反応条件

後処理

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
   その他The solvent was removed under reduced pressure
6. 6
   抽出the residue was extracted with EtOAc
7. 7
   洗浄The organic was washed with 2N HCl, H2O and brine
8. 8
   乾燥The organic was dried over anhydrous MgSO4
9. 9
   濃縮concentrated in vacuo

実験手順

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.

出典