Réaction #1884964

Équation de réaction

methyl iodide

n-BuLi

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

n-BuLi

→

solid

Rendement 81.0%

N-tert-Butyl-(1-methyl)cyclopropylsulfonamide

Rendement 81.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe dry ice bath was removed
2. 2
   Températureto warm to rt over a period of 1.5 h
3. 3
   TempératureThis mixture was then cooled to −78° C.
4. 4
   TempératureThe reaction mixture was warmed to rt
5. 5
   Températureto warm to rt overnight
6. 6
   Autrequenched with saturated NH4Cl (100 mL) at rt
7. 7
   ExtractionIt was extracted with EtOAc (100 mL)
8. 8
   LavageThe organic phase was washed with brine (100 mL)
9. 9
   Séchagedried (MgSO4)
10. 10
    Concentrationconcentrated in vacuo
11. 11
    Autreto give a yellow oil which
12. 12
    Autrewas crystallized from hexane

Mode opératoire

A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to −78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to −78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to −78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).

Source