Reaktion #1820347

Reaktionsgleichung

o-benzyloxybenzoic acid allylamide

phosgene

→

2-(o-Benzyloxypenyl)-pyrrole

Lösungsmittel

tetrahydrofuran benzene

—

20

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONafter distilling off the toluene under reduced pressure at 40° C. bath temperature
2. 2
   Filtrationthe solution is filtered through a pad of glass wool
3. 3
   workup.ADDITIONintroduced, in the course of 45 minutes, into an ice-
4. 4
   workup.ADDITION10 minutes after completion of the addition
5. 5
   workup.DISTILLATIONthe solvent is distilled off under reduced pressure
6. 6
   Sonstigethe residue is partitioned between methylene chloride and water
7. 7
   Extraktionthe water is extracted twice with methylene chloride

Vorschrift

2.7 (10 millimoles) of o-benzyloxybenzoic acid allylamide in 20 ml of a 20 per cent strength by weight solution of phosgene in tuluene are stirred, in the presence of 2 drops of dimethylformamide, at room temperature overnight. The residue which remains after distilling off the toluene under reduced pressure at 40° C. bath temperature is taken up in 30 ml of tetrahydrofuran, and the solution is filtered through a pad of glass wool and introduced, in the course of 45 minutes, into an ice-cooled solution of 4.0 g (30 millimoles) of potassium tert.-butylate in 60 ml of a 1:1 (by volume) tetrahydrofuran/benzene mixture, under argon as protective gas. 10 minutes after completion of the addition, the solvent is distilled off under reduced pressure, the residue is partitioned between methylene chloride and water, and the water is extracted twice with methylene chloride.

Quelle