Cyclopentanecarboxylic acid → HCID 22007883, compound

In 200 mL of methanol, was dissolved 8.91 g (75.4 mmol) of monomethyl malonate, and the resulting solution was mixed with 4.30 g (37.5 mmol) of magnesium ethoxide, and stirred for 4 hours at room temperature. The reaction solution was concentrated and the residue was dried under reduced pressure. In 120 mL of tetrahydrofuran, was dissolved 4.10 mL (37.7 mmol) of cyclopentanecarboxylic acid, and the resulting solution was mixed with 6.69 g (41.2 mmol) of carbonyldiimidazole, followed by stirring for 2.5 hours. The reaction solution was added to a dry magnesium salt and the resulting mixture was stirred at room temperature for 221 hours. The reaction solution was concentrated; the residue was mixed with 150 mL of 2 N hydrochloric acid, extracted with ethyl acetate, and washed with an aqueous sodium hydrogencarbonate solution and then saturated sodium chloride water. The resultant was dried over sodium sulfate anhydride, filtered, and concentrated. The residue was distilled (0.15 mmHg, 51 to 55° C.) to give 5.72 g (33.4 mmol, 88.8%) of methyl 2-cyclopentanecarbonylacetate as an anhydrous liquid. Similarly to Example 133, 2.32 g (8.39 mmol, 57.0%) of pale yellow crystals were obtained from 5.72 g (33.4 mmol) of methyl 2-cyclopentanecarbonylacetate.

1. concentrationThe reaction solution was concentrated
2. customthe residue was dried under reduced pressure
3. stirringby stirring for 2.5 hours
4. stirringthe resulting mixture was stirred at room temperature for 221 hours
5. concentrationThe reaction solution was concentrated
6. additionthe residue was mixed with 150 mL of 2 N hydrochloric acid
7. extractionextracted with ethyl acetate
8. washwashed with an aqueous sodium hydrogencarbonate solution
9. dry with materialThe resultant was dried over sodium sulfate anhydride
10. filtrationfiltered
11. concentrationconcentrated
12. distillationThe residue was distilled (0.15 mmHg, 51 to 55° C.)

ORD record

ord-2bf83d7491534ed1829beae670966c93

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06215016B1