Реакция #1884964

Уравнение реакции

methyl iodide

n-BuLi

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

n-BuLi

→

solid

Выход 81.0%

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

Выход 81.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe dry ice bath was removed
2. 2
   Температураto warm to rt over a period of 1.5 h
3. 3
   ТемператураThis mixture was then cooled to −78° C.
4. 4
   ТемператураThe reaction mixture was warmed to rt
5. 5
   Температураto warm to rt overnight
6. 6
   Другоеquenched with saturated NH4Cl (100 mL) at rt
7. 7
   ЭкстракцияIt was extracted with EtOAc (100 mL)
8. 8
   ПромывкаThe organic phase was washed with brine (100 mL)
9. 9
   Сушкаdried (MgSO4)
10. 10
    Концентрированиеconcentrated in vacuo
11. 11
    Другоеto give a yellow oil which
12. 12
    Другоеwas crystallized from hexane

Методика

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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