Reaction #350859

Reaction equation

hydrogen peroxide

(E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-one

lithium tri-sec-butyl borohydride

sodium hydroxide

→

above-identified compound

Yield 84.4%

(2RS,3SR,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol

Yield 84.4%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureunder cooling
2. 2
   workup.STIRRINGby stirring at the same temperature for 2 hours
3. 3
   Temperatureunder cooling with ice
4. 4
   workup.STIRRINGwith stirring
5. 5
   workup.STIRRINGby stirring at room temperature for one hour
6. 6
   ExtractionThe reaction solution was extracted by an addition of ethyl ether and water
7. 7
   WashThe organic layer was washed with a saturated sodium thiosulfate aqueous solution
8. 8
   Dryinga saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
9. 9
   FiltrationThe drying agent was filtered off
10. 10
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
11. 11
    OtherThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→5/1)

Procedure

4.78 g of (E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-one was dissolved in 30 ml of tetrahydrofuran, and 14.3 ml of a 1M tetrahydrofuran solution of lithium tri-sec-butyl borohydride was added at -78° C. under cooling with stirring, followed by stirring at the same temperature for 2 hours. To the reaction solution, 10 ml of a 2N sodium hydroxide aqueous solution was added under cooling with ice with stirring, and then, 15 ml of a 30% hydrogen peroxide aqueous solution was gradually dropwise added, followed by stirring at room temperature for one hour. The reaction solution was extracted by an addition of ethyl ether and water. The organic layer was washed with a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→5/1) to obtain 4.06 g of the above-identified compound.

Source