Réaction #45919

Équation de réaction

1-(2-chloroethyl)pyrrolidine hydrochloride

3-hydroxybenzaldehyde

Cs2CO3

→

3-(2-pyrrolidin-1-yl-ethoxy)benzaldehyde

Solvants

DMSO

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to rt
2. 2
   Autrethe reaction was quenched by cold H2O (50 mL)
3. 3
   Extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
4. 4
   LavageThe combined EtOAc extracts were washed with brine (3×50 mL)
5. 5
   Séchagedried (anhydrous Na2SO4)
6. 6
   AutreThe solvent was removed in vacuo

Mode opératoire

To a stirred solution of 3-hydroxybenzaldehyde (20 mmol) in DMSO (50 mL) at rt, solid Cs2CO3 (60 mmol) was added. 1-(2-chloroethyl)pyrrolidine hydrochloride (30 mmol) was added to the reaction mixture and heated to 90° C. for 9 h. After cooling to rt, the reaction was quenched by cold H2O (50 mL), and the resulting mixture was extracted with EtOAc (3×100 mL). The combined EtOAc extracts were washed with brine (3×50 mL) and dried (anhydrous Na2SO4). The solvent was removed in vacuo to afford crude 3-(2-pyrrolidin-1-yl-ethoxy)benzaldehyde.

Source