تفاعل #64388

معادلة التفاعل

HCl

n-BuLi

4-n-propylphenyl-t-butylsulfonamide

B(OiPr)3

→

titled compound

4-n-propylbenzene t-butylsulfonamide

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONTo the mixture, containing the bright red dianion at 0° C.
2. 2
   workup.STIRRINGthe mixture was stirred for 1 h
3. 3
   أخرىThe solvent was removed under reduced pressure
4. 4
   استخلاصthe residue was extracted with EtOAc
5. 5
   غسيلThe organic was washed with 2N HCl, H2O and brine
6. 6
   تجفيفThe organic was dried over anhydrous MgSO4
7. 7
   تركيزconcentrated in vacuo

الإجراء التجريبي

To a solution of 4-n-propylphenyl-t-butylsulfonamide (2.85 g, 11.2 mmoL) in anhydrous THF (20 mL) cooled to -40° C. under N2 was added 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright red dianion at 0° C., was added B(OiPr)3 (3.9 mL, 1.5 equiv). 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 crude material was used in subsequent steps without further purification.

المصدر