反応 #632007

反応方程式

n-butyllithium

methyl iodide

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

n-butyllithium

→

desired product

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

溶媒

THF

反応条件

後処理

1. 1
   その他The dry ice bath was removed
2. 2
   温度the reaction mixture was warmed to room temperature over a period of 1.5 hours
3. 3
   温度This mixture was cooled to −78° C.
4. 4
   温度The reaction mixture was warmed to room temperature
5. 5
   温度cooled to −78° C. over a period of 2 hours
6. 6
   温度The reaction mixture was warmed to room temperature overnight
7. 7
   その他quenched with saturated NH4Cl (100 mL) at room temperature
8. 8
   抽出extracted with ethyl acetate (100 mL)
9. 9
   洗浄The organic phase was washed with brine (100 mL)
10. 10
    乾燥dried (MgSO4)
11. 11
    ろ過filtered
12. 12
    濃縮concentrated in vacuo
13. 13
    その他to provide a yellow oil which
14. 14
    その他was crystallized from hexane

実験手順

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).

出典