Réaction #58666

Équation de réaction

1-(3-cyanophenyl)acetone

cyclobutyl bromide

cesium carbonate

→

title compound

3-(3-Cyanophenyl)-4-cyclobutyl-butan-2-one

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurewas cooled
2. 2
   Filtrationfiltered
3. 3
   AutreThe filtrate was partitioned between water and EtOAc
4. 4
   Extractionthe aqueous layer was extracted with EtOAc
5. 5
   LavageThe combined organic layer was washed with brine
6. 6
   Autredried
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was purified on a flash column

Mode opératoire

To a solution of 1.45 g (9.07 mmol) of 1-(3-cyanophenyl)acetone in 18 mL acetonitrile, 1.1 mL (9.5 mmol) cyclobutyl bromide and 5.91 g (18.1 mmol) cesium carbonate were added. After heating the solution in a 60° C. bath overnight, it was cooled and filtered. The filtrate was partitioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 5-10% EtOAc/hexane to isolate the title compound. 1H NMR: (500 MHz, CDCl3): δ 1.5-2.2 (m, 9H), 2.13 (s, 3H), 3.64 (m, 1H), 7.4-7.7 (m, 4H).

Source