Tetrahydrofuran → 4-(2,2,3-Trimethylcyclopentyl)butanoic acid

Temperature

110 °C

Ethyl 4-(2,2,3-trimethylcyclopentyl)butanoate (5 g, 22 mmol) was added to THF (25 ml) into a round bottom flask. Aqueous 1 N NaOH (25 ml) was then added to the flask and the reaction mixture was refluxed at 110° C. for 8 h. Upon completion of the reaction, the reaction mixture was diluted with 1 N NaOH (25 ml) and the aqueous layer washed twice with MTBE (50 ml×2). The aqueous layer was treated with aqueous 1.0 N HCl until it reached a pH of about 3 (for example from 2 to 4), then extracted three times with AcOEt (50 ml×3). The combined AcOEt extracts were concentrated in vacuo and purified via flash column chromatography with (0-40% gradient) to give 4-(2,2,3-trimethylcyclopentyl)butanoic acid as a colorless oil (3.82 g, 87%). The NMR data is indicated below.

1. customUpon completion of the reaction
2. washthe aqueous layer washed twice with MTBE (50 ml×2)
3. additionThe aqueous layer was treated with aqueous 1.0 N HCl until it
4. extractionextracted three times with AcOEt (50 ml×3)
5. concentrationThe combined AcOEt extracts were concentrated in vacuo
6. custompurified via flash column chromatography with (0-40% gradient)

ORD record

ord-df721f204b904b80b0134168452f33d3

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08409649B2