تفاعل #632007

معادلة التفاعل

n-butyllithium

methyl iodide

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

n-butyllithium

→

desired product

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe dry ice bath was removed
2. 2
   درجة الحرارةthe reaction mixture was warmed to room temperature over a period of 1.5 hours
3. 3
   درجة الحرارةThis mixture was cooled to −78° C.
4. 4
   درجة الحرارةThe reaction mixture was warmed to room temperature
5. 5
   درجة الحرارةcooled to −78° C. over a period of 2 hours
6. 6
   درجة الحرارةThe reaction mixture was warmed to room temperature overnight
7. 7
   أخرىquenched with saturated NH4Cl (100 mL) at room temperature
8. 8
   استخلاصextracted with ethyl acetate (100 mL)
9. 9
   غسيلThe organic phase was washed with brine (100 mL)
10. 10
    تجفيفdried (MgSO4)
11. 11
    ترشيحfiltered
12. 12
    تركيزconcentrated in vacuo
13. 13
    أخرىto provide a yellow oil which
14. 14
    أخرىwas crystallized from hexane

الإجراء التجريبي

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).

المصدر