반응 #46017

반응 방정식

4′-hydroxyacetophenone

potassium carbonate

mesylate

4-chlorophenethanol

methanesulfonyl chloride

→

1-{4-[2-(4-chlorophenyl)ethoxy]phenyl}ethanone

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   온도After cooling to rt
3. 3
   기타the reaction mixture was quenched with saturated sodium bicarbonate
4. 4
   workup.ADDITIONThe aqueous layer was poured into EtOAc (30 ml)
5. 5
   세척washed with water (2×15 ml) and brine (15 ml)
6. 6
   건조The organic layer was dried over magnesium sulfate
7. 7
   기타the solvent was removed in vacuuo

실험 절차

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%).

출처