Reacción #58666

Ecuación de reacción

1-(3-cyanophenyl)acetone

cyclobutyl bromide

cesium carbonate

→

title compound

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

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas cooled
2. 2
   Filtraciónfiltered
3. 3
   OtroThe filtrate was partitioned between water and EtOAc
4. 4
   Extracciónthe aqueous layer was extracted with EtOAc
5. 5
   LavadoThe combined organic layer was washed with brine
6. 6
   Otrodried
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified on a flash column

Procedimiento

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).

Fuente