methyl (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoate → (2Z,4E)-5-(Benzofuran-2-yl)-2-methoxy-2,4-pentadienoic acid

Participants

Reaction Steps

To a stirred solution of methyl (2Z,4E)-5-(benzofuran-2-yl)-2-methoxy-2,4-pentadienoate (1.0 g, 3.87 mmol) in EtOH/water 1/1 (80 ml) potassium hydroxide (0.43 g, 7.66 mmol) was added. The solution was refluxed for 1 hour, then it was cooled to RT and poured into water (200 ml). After acidification to pH 2 (1N HCl) the resulting suspension was extracted with EtOAc (3×50 ml). The organic phase was washed with water (2×30 ml), dried (MgSO4) and concentrated to give a yellow solid. This was repeatedly washed with CH2Cl2 and dried to give the pure title compound (0.80 g, 3.28 mmoles, yield 84.6%) as yellow crystals, m.p.=206°.

Provenance & Evidence