تفاعل #1884964

معادلة التفاعل

methyl iodide

n-BuLi

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

n-BuLi

→

solid

المردود 81.0%

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

المردود 81.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe dry ice bath was removed
2. 2
   درجة الحرارةto warm to rt over a period of 1.5 h
3. 3
   درجة الحرارةThis mixture was then cooled to −78° C.
4. 4
   درجة الحرارةThe reaction mixture was warmed to rt
5. 5
   درجة الحرارةto warm to rt overnight
6. 6
   أخرىquenched with saturated NH4Cl (100 mL) at rt
7. 7
   استخلاصIt was extracted with EtOAc (100 mL)
8. 8
   غسيلThe organic phase was washed with brine (100 mL)
9. 9
   تجفيفdried (MgSO4)
10. 10
    تركيزconcentrated in vacuo
11. 11
    أخرىto give a yellow oil which
12. 12
    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-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).

المصدر