Sodium Hydroxide → (2RS,3SR)-3-(3-benzyloxy-4-phenoxyphenyl)-5-phenylpentan-2-ol

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Reaction Steps

160 mg of (2RS,3SR)-2-acetoxy-3-(3-hydroxy-4-phenoxyphenyl)-5-phenylpentane was dissolved in 5 ml of methanol, and 2.5 ml of a 1N sodium hydroxide aqueous solution was added, followed by stirring at room temperature for 3.5 hours. The reaction solution was concentrated under reduced pressure, and then, the residue was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract solution was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in 1 ml of methyl ethyl ketone. The solution was added to a suspension having 116 mg of potassium carbonate preliminarily suspended in 3 ml of methyl ethyl ketone, and 58 μl of benzyl bromide was further added at room temperature, followed by stirring under heating at 100° C. for 4 hours. The reaction solution was left to cool, then neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract solution was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 173 mg (yield: 96%) of the above identified compound as a colorless oily substance.

Provenance & Evidence