Hydrogen Peroxide → (2RS,3RS)-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-ol

HRID 2287501Notes

Reaction equation

HRID 2287501 reaction equation
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[C:7](=[O:9])[CH3:8])[CH3:2].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO>O1CCCC1>[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[CH:7]([OH:9])[CH3:8])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 187052415,5-Diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-one

Product 1

HCID 18705240(2RS,3RS)-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-olYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 18.3 g of 5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-one in 200 ml of tetrahydrofuran, 65 ml of 1M tetrahydrofuran solution of lithium tri-sec-butylborohydride was added under cooling at -78° C. with stirring, and the resulting solution was stirred at the same temperature for 1 hour. To the reaction solution stirred and cooled with ice, 109 ml of 3N aqueous sodium hydroxide was added, and then 48 ml of 30% aqueous hydrogen peroxide was gradually added dropwise. The reaction solution was stirred at room temperature for 1 hour and partitioned between ethyl ether and water. The organic layer was washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1→3/1] to give 16.8 g of the title compound.

Workup

  1. stirringthe resulting solution was stirred at the same temperature for 1 hour
  2. stirringTo the reaction solution stirred
  3. additionwas added
  4. stirringThe reaction solution was stirred at room temperature for 1 hour
  5. custompartitioned between ethyl ether and water
  6. washThe organic layer was washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered off
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1→3/1]

Sources & evidence

ORD record
ord-0725e1d562f64764b953f794c4b2dc27
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

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