Réaction #8906

Équation de réaction

product

3-Acetyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridin-2 (1H)-one

cesium carbonate

1-bromopinacolone

→

title compound

1-{[3-Acetyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridin-2-yl]oxy}-3,3-dimethylbutan-2-one

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreTo a 25 mL rb flask equipped with a magnetic stir bar
2. 2
   workup.ADDITIONwas added
3. 3
   Autrethen partitioned between EtOAc and water
4. 4
   AutreThe organic layer was separated
5. 5
   Lavagewashed with 10% aq. NaHSO4, water, brine
6. 6
   Séchagedried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated
9. 9
   AutreThe residue was purified on s silica gel flash chromatography column
10. 10
    Lavageeluted with 0–10% EtOAc-hexane
11. 11
    AutreEvaporation of the purified fractions
12. 12
    Autredrying in vacuo

Mode opératoire

To a 25 mL rb flask equipped with a magnetic stir bar was added 0.309 g(0.86 mmol) of the product of Step A, 0.422 g (1.29 mmol) of cesium carbonate, 3 mL DMF and finally 145 μL of 1-bromopinacolone was added. The reaction mixture was stirred at room temperature for 1.5 h then partitioned between EtOAc and water. The organic layer was separated, washed with 10% aq. NaHSO4, water, brine, dried (MgSO4), filtered and evaporated. The residue was purified on s silica gel flash chromatography column eluted with 0–10% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Source