反应 #1884964

反应方程式

methyl iodide

n-BuLi

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

n-BuLi

→

solid

收率 81.0%

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

收率 81.0%

溶剂

THF

反应条件

后处理

1. 1
   其他The dry ice bath was removed
2. 2
   温度to warm to rt over a period of 1.5 h
3. 3
   温度This mixture was then cooled to −78° C.
4. 4
   温度The reaction mixture was warmed to rt
5. 5
   温度to warm to rt overnight
6. 6
   其他quenched with saturated NH4Cl (100 mL) at rt
7. 7
   萃取It was extracted with EtOAc (100 mL)
8. 8
   洗涤The organic phase was washed with brine (100 mL)
9. 9
   干燥dried (MgSO4)
10. 10
    浓缩concentrated in vacuo
11. 11
    其他to give a yellow oil which
12. 12
    其他was crystallized from hexane

实验过程

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).

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