Cyclohexene → methyl (S)-8-hydroxy-4-[2-(3-pyridyloxy)ethyl]octanoate

Participants

Reaction Steps

To a solution of methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate (1.1 g, 2.7 mmol) in ethanol (20 ml) is added cyclohexene (10.5 ml) followed by 20% palladium hydroxide on carbon (0.28 g). The mixture is heated at reflux for 18 hours. The catalyst is filtered off and washed with ethanol (3×10 ml). The solvent is evaporated and the residue purified by chromatography on silica gel using ethyl acetate as eluent to obtain methyl (S)-8-hydroxy-4-[2-(3-pyridyloxy)ethyl]octanoate; IR (CH2Cl2): 3600, 1732, 1282, 1230 cm-1.

Provenance & Evidence