Methanol → 3-Cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid (13.00 g, 37.77 mmol) in methanol (94 mL) was treated slowly with concentrated sulfuric acid (5 drops). The resulting reaction mixture was heated under reflux for 67 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 (300 mL). The organic phase was washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 100% hexanes then 19/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (13.18 g, 97%) as a yellow semi-solid: EI-HRMS m/e calcd for C15H19IO2 (M+) 358.0430, found 358.0434.

Provenance & Evidence