Tetrahydrofuran → 4-(2,2,3-Trimethyl-3-cyclopenten-1-yl)-2-butenoic acid

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Reaction Conditions

Reaction Steps

Ethyl 4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enoate (2.0 g, 9.0 mmol) was added to THF (10 ml) in a 50 ml round bottom flask. Aqueous 1 N NaOH (10 ml) was then added to the flask and the reaction mixture was refluxed at 83° C. for 19 h. Upon completion of the reaction, the reaction mixture was diluted with 1 N NaOH (10 ml) and the aqueous layer was washed twice with MTBE (10 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 (10 ml×3). The combined AcOEt extracts were concentrated in vacuo and purified via flash column chromatography with MTBE/Hexanes (5-20% gradient) to give 4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enoic acid (1.58 g) as a viscous oil (1.58 g, 90%). The NMR data is indicated below.

Provenance & Evidence