Tetrahydrofuran → 1-(4-Chlorobutyl)cyclopentanecarboxylic acid

Temperature

42.5 °C

To a solution of 1-(4-chlorobutyl)cyclopentane carboxylic acid methyl ester (30 mmol, 6.56 g) in a mixture of THF (60 mL) and methanol (60 mL) was added 1 N sodium hydroxide (60 mL). The mixture was heated to 40-45° C. for 15 h at which point TLC analysis of the reaction mixture indicated the absence of starting material and it was cooled to room temperature. The solvent was removed under vacuum and the residue was diluted with water (100 mL) and extracted with ether (2×100 mL) to remove any neutral impurities. Then, the basic aqueous layer was acidified with 1 N hydrochloric acid and the product was extracted with ethyl acetate (2×75 mL). The combined extracts were washed with brine solution and were dried over anhydrous sodium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the residue was purified by silica gel column chromatography to afford 4.2 g (68%) of 1-(4-chlorobutyl)cyclopentane carboxylic acid as a liquid and 1.3 g (22%) of 1-[4-(methoxy)butyl]cyclopentane carboxylic acid as a viscous oil. HR MS (C11H20O3): Obs mass, 200.0175. Calcd mass, 200.0143 (M+).

1. temperaturewas cooled to room temperature
2. customThe solvent was removed under vacuum
3. additionthe residue was diluted with water (100 mL)
4. extractionextracted with ether (2×100 mL)
5. customto remove any neutral impurities
6. extractionthe product was extracted with ethyl acetate (2×75 mL)
7. washThe combined extracts were washed with brine solution
8. dry with materialwere dried over anhydrous sodium sulfate
9. filtrationAfter filtration of the drying agent
10. concentrationthe solution was concentrated under vacuum
11. customthe residue was purified by silica gel column chromatography

ORD record

ord-48fcf3a812ac4ffbb1d559bfb22a2b50

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06806365B2