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 (7.18 g, 20.86 mmol) in methanol (150 mL) was treated with a catalytic amount of concentrated sulfuric acid (7 drops). The reaction mixture was heated at 70° C. for 18 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The residue was partitioned between ethyl acetate (400 mL) and a saturated aqueous sodium bicarbonate solution (400 mL). The aqueous layer was extracted with ethyl acetate (1×400 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×400 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (7.24 g, 96.9%) as an off-white solid: mp 51-54° C.; EI-HRMS m/e calcd for C15H19IO2 (M+) 358.0429, found 358.0419.

Provenance & Evidence