Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(3,4-Dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3,4-dichloro-phenyl)-3-[2-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester (prepared as in Example 24, 2.3 g, 5.73 mmol) in ethanol (57.3 mL) at 25° C. was treated with pyridinium p-toluenesulfonate (144 mg, 0.57 mmol). The resulting solution was heated under reflux for 18 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 2-(3,4-dichloro-phenyl)-3-(2-hydroxy-cyclopentyl)-propionic acid methyl ester (1.84 g, 100%) as a clear oil: EI-HRMS m/e calcd for C15H18Cl2O3 (M+Na)+ 339.0527. found 339.0528.

Provenance & Evidence