Methanol → 2-Biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 2-biphenyl-4-yl-3-cyclopentylpropionic acid (192.3 mg, 0.653 mmol) in methanol (3.3 mL) was treated slowly with concentrated sulfuric acid (1 drop). The resulting reaction mixture was heated under reflux for 24 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate (50 mL). The organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL), water (1×100 mL), and a saturated aqueous sodium chloride solution (1×100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 9/1 hexanes/ethyl acetate) afforded 2-biphenyl-4-yl-3-cyclopentylpropionic acid methyl ester (191.5 mg, 95%) as a yellow oil: EI-HRMS m/e calcd for C21H24O2 (M+) 308.1776, found 308.1774.

Provenance & Evidence