Reaktion #1884963

ord-feb3d9d0a6174fd686704936a68f14cb

Reaktionsgleichung

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

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe volatiles were removed in vacuo
  2. 2
    SonstigeThe residue was partitioned between EtOAC and water (200 mL, 200 mL)
  3. 3
    WaschenThe separated organic phase was washed with brine
  4. 4
    Trocknendried over Na2SO4
  5. 5
    Filtrationfiltered
  6. 6
    Einengenconcentrated in vacuo
  7. 7
    SonstigeThe residue was recrystallized from hexane

Vorschrift

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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08343477B2uspto-grants-2013_01