تفاعل #1884963

ord-feb3d9d0a6174fd686704936a68f14cb

معادلة التفاعل

CC(C)(C)NS(=O)(=O)CCCCl
N-tert-butyl-(3-chloro)propylsulfonamide
[Li][CH2]CCC
n-BuLi
CC(C)(C)NS(=O)(=O)C1CC1
desired product
المردود 56.4%
CC(C)(C)NS(=O)(=O)C1CC1
Cyclopropanesulfonic Acid tert-Butylamide
المردود 56.4%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe volatiles were removed in vacuo
  2. 2
    أخرىThe residue was partitioned between EtOAC and water (200 mL, 200 mL)
  3. 3
    غسيلThe separated organic phase was washed with brine
  4. 4
    تجفيفdried over Na2SO4
  5. 5
    ترشيحfiltered
  6. 6
    تركيزconcentrated in vacuo
  7. 7
    أخرىThe residue was recrystallized from hexane

الإجراء التجريبي

To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08343477B2uspto-grants-2013_01