Sodium Hydroxide → 2-(3,5-Dihydroxy-phenyl)-4-methyl-pentanoic acid methyl ester

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Reaction Steps

10% Pd/C (Aldrich cat no 205699, 214 mg) was added to a stirred solution of 2-(3,5-bis-benzyloxyphenyl)-4-methyl-pent-4-enoic acid methyl ester (2.14 g, 5.1 mmol) and NaOH (225 mg, 5.6 mmol) in MeOH (30 mL) at room temperature. Stirring was continued for 2 h under H2 (1 atm.) then the mixture was filtered through Celite, concentrated in vacuo, suspended in water (15 mL) and adjusted to pH 2 with 1M HCl. The mixture was extracted with DCM (3×60 mL); the combined organic layer washed with brine (20 mL), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica, 0-20% EtOAc in petroleum ether) to give the title product as a white syrup (1.1 g, 90%).

Provenance & Evidence