Reaktion #3698

Reaktionsgleichung

sodium hydride

pyrrole-2-carboxaldehyde

ethyl 4-nitro-3-bromomethylbenzoate

→

desired product

Ausbeute 83.9%

1-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde

Ausbeute 83.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Sonstigecarefully quenched with water
3. 3
   ExtraktionThe reaction mixture is extracted with chloroform which
4. 4
   Waschenis washed with water
5. 5
   Trocknendried with Na2SO4
6. 6
   Einengenconcentrated in vacuo

Vorschrift

To a stirred slurry of 2.2 g of sodium hydride (60% in oil, washed with hexane) in tetrahydrofuran is added at 0° C. a solution of 4.5 g of pyrrole-2-carboxaldehyde in 25 ml of tetrahydrofuran. After the addition is complete, a solution of 15 g of ethyl 4-nitro-3-bromomethylbenzoate in 30 ml of dry tetrahydrofuran is slowly added under nitrogen. The reaction mixture is stirred at 20° C. for 8 hours and carefully quenched with water. The reaction mixture is extracted with chloroform which is washed with water, dried with Na2SO4 and concentrated in vacuo to give 12 g of the desired product as a solid; mass spectrum (M+ H)349.

Quelle