반응 #632007

반응 방정식

n-butyllithium

methyl iodide

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

n-butyllithium

→

desired product

N-tert-butyl-(1-methyl)cyclopropyl-sulfonamide

용매

THF

반응 조건

후처리

1. 1
   기타The dry ice bath was removed
2. 2
   온도the reaction mixture was warmed to room temperature over a period of 1.5 hours
3. 3
   온도This mixture was cooled to −78° C.
4. 4
   온도The reaction mixture was warmed to room temperature
5. 5
   온도cooled to −78° C. over a period of 2 hours
6. 6
   온도The reaction mixture was warmed to room temperature overnight
7. 7
   기타quenched with saturated NH4Cl (100 mL) at room temperature
8. 8
   추출extracted with ethyl acetate (100 mL)
9. 9
   세척The organic phase was washed with brine (100 mL)
10. 10
    건조dried (MgSO4)
11. 11
    여과filtered
12. 12
    농축concentrated in vacuo
13. 13
    기타to provide a yellow oil which
14. 14
    기타was crystallized from hexane

실험 절차

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-butyllithium (17.6 mL, 44 mmol, 2.5M in hexane) slowly. The dry ice bath was removed and the reaction mixture was warmed to room temperature over a period of 1.5 hours. This mixture was cooled to −78° C. and a solution of n-butyllithium (20 mmol, 8 mL, 2.5M in hexane) was added. The reaction mixture was warmed to room temperature, cooled to −78° C. over a period of 2 hours, and treated with a neat solution of methyl iodide (5.68 g, 40 mmol). The reaction mixture was warmed to room temperature overnight, then quenched with saturated NH4Cl (100 mL) at room temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil which was crystallized from hexane to provide the desired 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 (br s, 1H).

출처