Reaktion #46017

Reaktionsgleichung

4′-hydroxyacetophenone

potassium carbonate

mesylate

4-chlorophenethanol

methanesulfonyl chloride

→

1-{4-[2-(4-chlorophenyl)ethoxy]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 with saturated sodium bicarbonate
4. 4
   workup.ADDITIONThe aqueous layer was poured into EtOAc (30 ml)
5. 5
   Waschenwashed with water (2×15 ml) and brine (15 ml)
6. 6
   TrocknenThe organic layer was dried over magnesium sulfate
7. 7
   Sonstigethe solvent was removed in vacuuo

Vorschrift

To a stirred solution of 4′-hydroxyacetophenone (4 mmol) in DMF (10 mL) at rt, solid potassium carbonate (12.0 mmol) was added. 4-chlorophenthoxy mesylate (prepared from the 4-chlorophenethanol and methanesulfonyl chloride) (4.4 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 with saturated sodium bicarbonate. The aqueous layer was poured into EtOAc (30 ml) and washed with 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-[2-(4-chlorophenyl)ethoxy]phenyl}ethanone. The crude alkylated product was purified by silica gel chromatography and the pure product obtained from 10% EtOAc/hexanes (yield 70%).

Quelle