Hydrochloric Acid → 4-n-Propylbenzene t-butylsulfonamide

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.

1. additionTo the mixture, containing the bright red dianion at 0° C.
2. stirringthe mixture was stirred for 1 h
3. customThe solvent was removed under reduced pressure
4. extractionthe residue was extracted with EtOAc
5. washThe organic was washed with 2N HCl, H2O and brine
6. dry with materialThe organic was dried over anhydrous MgSO4
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-c499ed1d523643029c3e0d4e817a16f2

Quelldatensatz

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05412097