Reaktion #362118

Reaktionsgleichung

sodium hydride

1-carboethoxy-2-benzimidazolinone

product

ethyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-(3,4-methylenedioxyphenyl)acetate

→

title compound

Ausbeute 64.0%

1-[4-(1-carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dichlorophenylmethyl]-3-carboethoxy-2-benzimidazolinone

Ausbeute 64.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturgently warmed with a heat gun until the solids
2. 2
   workup.DISSOLUTIONhad dissolved
3. 3
   workup.STIRRINGthe reaction mixture was stirred for an additional 1.5 hours
4. 4
   SonstigeThe mixture was then quenched with 5% aqueous ammonium chloride
5. 5
   Extraktionextracted into ethyl acetate
6. 6
   SonstigeThe organic layer was separated
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    Sonstigethe residue was purified on a silica gel flash chromatography column
11. 11
    Wascheneluted with 30% EtOAc-hexane
12. 12
    SonstigeEvaporation of the purified fractions
13. 13
    Sonstigedrying in vacuo

Vorschrift

To a solution of 0.048 g (0.24 mmol) of 1-carboethoxy-2-benzimidazolinone dissolved in 0.5 mL DMF was added 0.010 g (0.26 mmol) of a 60% oil dispersion of sodium hydride and the resulting mixture was stirred under a nitrogen atmosphere and gently warmed with a heat gun until the solids had dissolved. A solution of the product of step B in 1.0 mL DMF was then added and the reaction mixture was stirred for an additional 1.5 hours. The mixture was then quenched with 5% aqueous ammonium chloride and extracted into ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and 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 0.088 g (64%) of the title compound.

Quelle