反応 #1884964

反応方程式

methyl iodide

n-BuLi

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

n-BuLi

→

solid

収率 81.0%

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

収率 81.0%

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
   その他quenched with saturated NH4Cl (100 mL) at rt
7. 7
   抽出It was extracted with EtOAc (100 mL)
8. 8
   洗浄The organic phase was washed with brine (100 mL)
9. 9
   乾燥dried (MgSO4)
10. 10
    濃縮concentrated in vacuo
11. 11
    その他to give a yellow oil which
12. 12
    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-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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