Reaktion #362127

Reaktionsgleichung

1-carboethoxy-2-benzimidazolinone

cesium carbonate

product

ethyl 2-(4-bromomethylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

→

title compound

Ausbeute 58.0%

1-[4-(1-carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-3-carboethoxy-2-benzimidazolinone

Ausbeute 58.0%

Lösungsmittel

DMF

DMF

citric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred for an additional 1 hour
2. 2
   Extraktionextracted into ethyl acetate
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with saturated sodium bicarbonate and brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   Sonstigethe residue was purified on a silica gel flash chromatography column
9. 9
   Wascheneluted with 30% EtOAc-hexane
10. 10
    SonstigeEvaporation of the purified fractions
11. 11
    Sonstigedrying in vacuo

Vorschrift

To a solution of 0.020 g (0.10 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 250 gL DMF was added 0.035 g (0.11 mmol) of cesium carbonate and the resulting suspension was stirred under a nitrogen atmosphere for 10 minutes. A solution of the product of step B in 300 aL DMF was then added and the reaction mixture was stirred for an additional 1 hour. The mixture was suspended in 10% aqueous citric acid and extracted into ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered, evaporated, and the residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.029 g (58%) of the title compound.

Quelle