Methyl iodide → 3-Oxo-cyclopentanecarboxylic acid methyl ester

Temperature

0 °C

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-oxocyclopentane-1-carboxylic acid (1.0 g, 7.80 mmol, 1.00 equiv), potassium carbonate (1.62 g, 11.72 mmol, 1.50 equiv), Acetone (20 mL). This was followed by the addition of iodomethane (11.1 g, 78.20 mmol, 10.02 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at 60° C. in an oil bath. The reaction progress was monitored by GCMS. The solids were collected by filtration. The filtrate was concentrate. The resulting mixture was diluted with 10 mL of H2O. The resulting solution was extracted with 3×10 mL of ether and the organic layers combined and dried over anhydrous sodium sulfate and concentrated. This resulted in 1.0 g (crude) of methyl 3-oxocyclopentane-1-carboxylate as yellow oil. The crude could be used for the next step directly.

1. customInto a 100-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred overnight at 60° C. in an oil bath
4. filtrationThe solids were collected by filtration
5. concentrationThe filtrate was concentrate
6. additionThe resulting mixture was diluted with 10 mL of H2O
7. extractionThe resulting solution was extracted with 3×10 mL of ether
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated
10. customThis resulted in 1.0 g (crude) of methyl 3-oxocyclopentane-1-carboxylate as yellow oil

ORD record

ord-5322de29e37d42cab2fe5dfab853b747

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1