Réaction #947

ord-031db419b85e49eb8266022d09028e45

Équation de réaction

O=S(=O)(O)Cl
Chlorosulphonic acid
CC=CCC(N)(CC)CO
product
CC=CCC(N)(CC)CO
(+-)-2-Amino-2-ethylhex-4-en-1-ol
CC=CCC1(CC)CN1
desired product
Rendement 57.0%
CC=CCC1(CC)CN1
(+-)-2-But-2-enyl-2-ethylaziridine
Rendement 57.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONWhen addition
  2. 2
    FiltrationThe resulting crystals were filtered off
  3. 3
    Lavagewashed with acetonitrile/pet. ether
  4. 4
    Autredried
  5. 5
    workup.ADDITIONtaken up in a mixture of 50%
  6. 6
    workup.DISTILLATIONKOH (100 mL) and water (55 mL) and distilled over KOH

Mode opératoire

Chlorosulphonic acid (18 mL) was added to a solution of the product from step (e) (32.3 g) in acetonitrile (100 ml) at least 9° C. When addition was complete, the mixture was warmed to room temperature. The resulting crystals were filtered off, washed with acetonitrile/pet. ether, dried, taken up in a mixture of 50% w/v aqu. KOH (100 mL) and water (55 mL) and distilled over KOH to give the desired product as a colourless oil (16.1 g). 1H NMR consistent with the proposed structure.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723458uspto-grants-1998_03