Réaction #1552091

Équation de réaction

potassium carbonate

methyl 2-oxocyclopentanecarboxylate

1-bromo-3,3-dimethylbutane

→

methyl 1-(3,3-dimethylbutyl)-2-oxocyclopentanecarboxylate

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 14 hours
2. 2
   Filtrationfiltered off through Celite
3. 3
   ConcentrationThe product is concentrated under reduced pressure
4. 4
   Autrepurified by column chromatography (silica gel 100-200 mesh, mobile phase: ethyl acetate 5%/petroleum ether)

Mode opératoire

117.0 g (846.0 mmol) of potassium carbonate are added to a solution consisting of 40.0 g (281.7 mmol) of methyl 2-oxocyclopentanecarboxylate in 160 ml of dry toluene. 93 g (563.4 mmol) of 1-bromo-3,3-dimethylbutane are then added dropwise, and the mixture is stirred at reflux for 14 hours. After the reaction has ended the mixture is cooled to room temperature and filtered off through Celite. The product is concentrated under reduced pressure and purified by column chromatography (silica gel 100-200 mesh, mobile phase: ethyl acetate 5%/petroleum ether). This gives 48 g (75% of theory) of methyl 1-(3,3-dimethylbutyl)-2-oxocyclopentanecarboxylate.

Source