Reaktion #168707

Reaktionsgleichung

HCl

N-[1-(3-bromo-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide

t-BuOH

potassium tert-butoxide

→

title compound

5-(3-Bromo-phenyl)-5-hydroxymethyl-morpholin-3-one

Lösungsmittel

TBME

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Filtrationthe precipitate was filtered off
3. 3
   SonstigeThe organic phase of the filtrate was separated
4. 4
   Trocknendried with sodium sulfate
5. 5
   Sonstigechromatographed on silica gel (EtOAc/MeOH 1-2%)

Vorschrift

A suspension of N-[1-(3-bromo-phenyl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide (3.24 g, 10.04 mmol) and 35 ml of t-BuOH was treated with potassium tert-butoxide (1.127 g, 10.04 mmol). The mixture was heated at reflux for 1 h and neutralized with 10 ml of 1N HCl. Water and TBME were added, and the precipitate was filtered off. The organic phase of the filtrate was separated, dried with sodium sulfate and chromatographed on silica gel (EtOAc/MeOH 1-2%) to give the title compound in the form of a colourless solid. TLC (EtOAc/MeOH 1%): Rf=0.23, HPLC: RtH2=2.839 min; 1H-NMR (400 MHz, CD3OD): 7.70 (s, 1H), 7.53-7.47 (m, 2H), 7.35 (t, 1H), 4.17 (s, 2H), 4.08 (d, 1H), 3.98 (d, 1H), 3.91 (d, 1H), 3.87 (d, 1H); MS: 287, 289 [(M+H)+].

Quelle