Reaktion #168696

Reaktionsgleichung

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

potassium tert-butoxide

→

title compound

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

Lösungsmittel

tert-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 30 min
2. 2
   Temperaturafter cooling
3. 3
   Sonstigequenched with water
4. 4
   Sonstigeevaporated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in EtOAc (500 ml)
6. 6
   Waschenwashed with water and brine
7. 7
   TrocknenThe organic phase was dried with Na2SO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto yield the crude title compound
10. 10
    SonstigeThe crude product was purified by chromatography on silica gel (PE/EtOAc=20:1 to 1:1)

Vorschrift

The crude N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (70 g, 230 mmol) was dissolved in tert-butanol (1 l). The solution was treated with portions of potassium tert-butoxide (52 g, 460 mmol). The mixture was refluxed for 30 min, after cooling quenched with water and evaporated. The residue was dissolved in EtOAc (500 ml) and washed with water and brine. The organic phase was dried with Na2SO4 and concentrated in vacuo to yield the crude title compound. The crude product was purified by chromatography on silica gel (PE/EtOAc=20:1 to 1:1) to give the title compound in the form of a grey solid. 1H-NMR (400 MHz, DMSO-d6): 8.66 (s, 1H), 7.60 (s, 1H), 7.48 (d, 1H), 7.44 (d, 1H), 7.34 (t, 1H), 4.02 (s, 2H), 3.92 (d, 1H), 3.68 (d, 1H), 1.38 (s, 3H).

Quelle