4'-Hydroxyacetophenone → 1-{4-[2-(4-Chlorophenyl)ethoxy]phenyl}ethanone

Temperatur

80 °C

To a stirred solution of 4′-hydroxyacetophenone (1.2 mmol) in DMF (10 mL) at rt, solid potassium carbonate (3.0 mmol) was added. 4-chlorophenethyl mesylate (1.0 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 quenched by removing solvent in vacuuo and treating the residue with saturated sodium bicarbonate. The aqueous layer was poured into EtOAc (20 ml) and washed with H2O (2×10 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 acetophenone was used for further transformation without any purification or after purifying using silica gel column chromatography.

1. temperatureAfter cooling to rt
2. customthe reaction mixture was quenched
3. customby removing solvent in vacuuo
4. additiontreating the residue with saturated sodium bicarbonate
5. additionThe aqueous layer was poured into EtOAc (20 ml)
6. washwashed with H2O (2×10 ml) and brine (15 ml)
7. dry with materialThe organic layer was dried over magnesium sulfate
8. customthe solvent was removed in vacuuo

ORD-Eintrag

ord-8666a1d26c2f46d0895a0a4c6498fbc2

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07737285B2