Reaktion #45977

Reaktionsgleichung

4′-hydroxyacetophenone

potassium carbonate

mesylate

3-diethylamino-1-propanol

methanesulfonyl chloride

→

1-{4-[3-(diethylamino)propoxy]phenyl}ethanone

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   TemperaturAfter cooling to rt
3. 3
   Sonstigethe reaction mixture was quenched
4. 4
   workup.ADDITIONby treating the mixture with saturated sodium bicarbonate
5. 5
   workup.ADDITIONThe aqueous layer was poured into EtOAc (100 mL)
6. 6
   Waschenwashed with H2O (2×50 mL) and brine (50 mL)
7. 7
   TrocknenThe organic layer was dried over sodium sulfate
8. 8
   Sonstigethe solvent was removed in vacuuo

Vorschrift

To a stirred solution of 4′-hydroxyacetophenone (91 mmol) in DMF (80 mL) at rt, solid potassium carbonate (153 mmol) was added. The mesylate prepared from 3-diethylamino-1-propanol and methanesulfonyl chloride (76 mmol) was added to the reaction mixture and heated to 80° C. until completion according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was quenched by treating the mixture with saturated sodium bicarbonate. The aqueous layer was poured into EtOAc (100 mL) and washed with H2O (2×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[3-(diethylamino)propoxy]phenyl}ethanone. The crude alkylated product was used for further transformation after purifying using silica gel column chromatography (1-4% MeOH/DCM).

Quelle