Реакция #632007

Уравнение реакции

n-butyllithium

methyl iodide

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

n-butyllithium

→

desired product

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

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe dry ice bath was removed
2. 2
   Температураthe reaction mixture was warmed to room temperature over a period of 1.5 hours
3. 3
   ТемператураThis mixture was cooled to −78° C.
4. 4
   ТемператураThe reaction mixture was warmed to room temperature
5. 5
   Температураcooled to −78° C. over a period of 2 hours
6. 6
   ТемператураThe reaction mixture was warmed to room temperature overnight
7. 7
   Другоеquenched with saturated NH4Cl (100 mL) at room temperature
8. 8
   Экстракцияextracted with ethyl acetate (100 mL)
9. 9
   ПромывкаThe organic phase was washed with brine (100 mL)
10. 10
    Сушкаdried (MgSO4)
11. 11
    Фильтрацияfiltered
12. 12
    Концентрированиеconcentrated in vacuo
13. 13
    Другоеto provide a yellow oil which
14. 14
    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-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).

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