Reaktion #444483

Reaktionsgleichung

2-amino-3-nitrophenol

(2S)-(+)-glycidyl 3-nitrobenzenesulfonate

K2CO3

→

(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 18 hours
2. 2
   Filtrationthe solids were filtered
3. 3
   Einengenand the filtrate concentrated in vacuo to dryness
4. 4
   SonstigeThe resulting solids were partitioned between chloroform and water
5. 5
   Extraktionthe aqueous layer extracted once with chloroform
6. 6
   Sonstigedried over Na2 SO4
7. 7
   Einengenconcentrated in vacuo to 8.0 g (99%) of an orange solid
8. 8
   Sonstigeso the material was used without further purification

Vorschrift

A solution of 2-amino-3-nitrophenol (5.95 g, 38.6 mmol) and (2S)-(+)-glycidyl 3-nitrobenzenesulfonate (10.0 g, 38.6 mmol) in 150 mL of acetone was treated with 1.1 equivalents of K2CO3 (5.86 g, 42.4 mmol) and stirred at reflux for 18 hours. The suspension was cooled to ambient temperature; the solids were filtered; and the filtrate concentrated in vacuo to dryness. The resulting solids were partitioned between chloroform and water, and the aqueous layer extracted once with chloroform. The organic layers were combined and dried over Na2 SO4 and concentrated in vacuo to 8.0 g (99%) of an orange solid. TLC (Rf =0.5, CHCl3) and NMR indicated >95% purity, so the material was used without further purification. NMR.

Quelle