Reaktion #53515

ord-f4b14f780c4148528ec5549cc4115d8e

Reaktionsgleichung

Nc1c(O)cccc1[N+](=O)[O-]
2-amino-3-nitrophenol
O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(S)-(+)-glycidyl 3-nitrobenzenesulfonate
O=C([O-])[O-].[K+].[K+]
K2CO3
→
Nc1c(OC[C@@H]2CO2)cccc1[N+](=O)[O-]
title product
Ausbeute 84.3%
Nc1c(OC[C@@H]2CO2)cccc1[N+](=O)[O-]
2-Amino-3-nitro-1-((2S)-2,3-epoxypropoxy)benzene
Ausbeute 84.3%

Edukte

Nc1c(O)cccc1[N+](=O)[O-]
2-amino-3-nitrophenol
O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(S)-(+)-glycidyl 3-nitrobenzenesulfonate
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe mixture is refluxed for 18 hours
  2. 2
    FiltrationFiltration
  3. 3
    Sonstigethe solvent is evaporated under reduced pressure
  4. 4
    Sonstigethe crude product is purified by flash chromatography, elution
  5. 5
    SonstigeThe solid product obtained
  6. 6
    Sonstigeis triturated in ethyl ether

Vorschrift

5 g (0.032 mol) of 2-amino-3-nitrophenol, 8 g (0.032 mol) of (S)-(+)-glycidyl 3-nitrobenzenesulfonate and 8.9 g of K2CO3 are mixed in 80 ml of acetone and the mixture is refluxed for 18 hours. Filtration is carried out, the solvent is evaporated under reduced pressure and the crude product is purified by flash chromatography, elution being carried out with a 7/3 cyclohexane/ethyl acetate mixture. The solid product obtained is triturated in ethyl ether and 5.67 g of the title product are obtained. M.p.: 107-109°. αD+28.1 (c=0.5%, MeOH).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858629B1uspto-grants-2005_02