Reaktion #3059

Reaktionsgleichung

O-benzylhydroxylamine hydrochloride

bromoacetyl bromide

diisopropylethylamine

→

title compound

Ausbeute 52.0%

Bromo-N-(benzyloxyl)acetamide

Ausbeute 52.0%

Lösungsmittel

ethyl acetate

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe aqueous layer was separated
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane

Vorschrift

To a 0° C. solution of O-benzylhydroxylamine hydrochloride (1.6 g, 10 mmol) in THF (40 mL) was added bromoacetyl bromide (871 μL, 10 mmol) and diisopropylethylamine (3.5 mL, 20 mmol). The reaction mixture was warmed to room temperature overnight and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane to give 1.27 g (52%) of the title compound.

Quelle