Reacción #632006

Ecuación de reacción

N-tert-butyl-(3-chloro)propylsulfonamide

n-butyllithium

→

desired product

Rendimiento 56.4%

Cyclopropanesulfonic Acid Tert-Butylamide

Rendimiento 56.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo
2. 2
   OtroThe concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL)
3. 3
   LavadoThe organic phase was washed with brine
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe concentrate was recrystallized from hexane

Procedimiento

To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-butyllithium (2.5M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reaction mixture was warmed to room temperature over a period of 1 hour and concentrated in vacuo. The concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The concentrate was recrystallized from hexane to provide the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (br, 1H).

Fuente