Reaktion #45964

Reaktionsgleichung

mesylate

N,N-diethyaminopropanol

methanesulfonyl chloride

4′-hydroxyacetophenone

potassium carbonate

→

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

Ausbeute 50.0%

Lösungsmittel

water

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   TemperaturAfter cooling to rt
3. 3
   WaschenThe combined organic layers were washed with saturated sodium bicarbonate (2×15 ml), water (2×15 ml) and brine (15 ml)
4. 4
   TrocknenThe organic layer was dried over magnesium sulfate
5. 5
   Sonstigethe solvent was removed in vacuuo

Vorschrift

To a stirred solution of 4′-hydroxyacetophenone (2.2 mmol) in DMF (10 mL) at rt, solid potassium carbonate (8.0 mmol) was added. The mesylate of N,N-diethyaminopropanol (prepared from the corresponding alcohol and methanesulfonyl chloride) (2.0 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 diluted with water and the product was isolated in EtOAc. The combined organic layers were washed with saturated sodium bicarbonate (2×15 ml), water (2×15 ml) and brine (15 ml). The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[3-(diethylamino)propoxy]phenyl}ethanone. The crude alkylated product was purified using silica gel column chromatography. Pure product was obtained with 2-3% MeOH/DCM. (yield 50-60%)

Quelle