Hydrogen Peroxide → HCID 70281683, compound

Participants

Reaction Conditions

Reaction Steps

1.95 of the ketone thus obtained was dissolved in 62 ml of tetrahydrofuran, and 7.0 ml of a 1M tetrahydrofuran solution of lithium tri-sec-butyl borohydride was added under cooling to -78° C. with stirring, followed by stirring at the same temperature for 30 minutes. To the reaction solution, 20 ml of a 0.5N sodium hydroxide aqueous solution was added, and then 10 ml of a 30% hydrogen peroxide aqueous solution was dropwise added thereto. After the dropwise addition, the mixture was stirred at room temperature for 30 minutes. The reaction solution was extracted by an addition of water and ethyl acetate, followed by conventional post-treatment. Then, purification was conducted by medium pressure liquid chromatography (hexane/ethyl acetate=5/1) to obtain 1.91 g of (2S*,3S*,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol.

Provenance & Evidence