Potassium Carbonate → HCID 178517420, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trimethylaluminum in toluene (2M, 25 mL, 50 mmol) was added slowly under nitrogen to a suspension of ammonium chloride (2.9 g, 54 mmol) in anhydrous toluene at 0° C.-5° C. The mixture was then stirred at a temperature in the range of 15° C. to 40° C. for 20 min before addition of a solution of cyclopentanecarbonitrile (3.13 mL, 30 mmol) in toluene. The resulting mixture was then heated at 80° C. under stirring for 10 hours. Thereafter, the mixture was cooled to a temperature in the range of 15° C. to 40° C. MeOH was slowly added to quench the reaction and stirred at a temperature in the range of 15° C. to 40° C. for 1 hour. Thereafter, the precipitate was filtered and washed with MeOH (3×30 mL). The filtrate and the washings were combined and concentrated under reduced pressure. After drying under vacuum, the crude solid (3.5 g) was dissolved in anhydrous EtOH (20 mL). Methyl-2-oxo-cyclopentanecarboxylate (3.1 mL, 25 mmol) and K2CO3 (4.14 g, 30 mmol) were added sequentially to this solution and the mixture was heated to reflux for a period over 6-15 hours. Thereafter, volatiles were evaporated under reduced pressure and the mixture was diluted with ice-water under stirring. The resultant precipitate was filtered, washed thoroughly with water followed by ether and dried under vacuum (4.6 g, 95.4% yield).

Provenance & Evidence