Реакция #1884963

ord-feb3d9d0a6174fd686704936a68f14cb

Уравнение реакции

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
Выход 56.4%
CC(C)(C)NS(=O)(=O)C1CC1
Cyclopropanesulfonic Acid tert-Butylamide
Выход 56.4%

Реагенты

Нет

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThe volatiles were removed in vacuo
  2. 2
    ДругоеThe residue was partitioned between EtOAC and water (200 mL, 200 mL)
  3. 3
    ПромывкаThe separated organic phase was washed with brine
  4. 4
    Сушкаdried over Na2SO4
  5. 5
    Фильтрацияfiltered
  6. 6
    Концентрированиеconcentrated in vacuo
  7. 7
    ДругоеThe residue was recrystallized from hexane

Методика

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%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08343477B2uspto-grants-2013_01