Hydrogen Peroxide → HCID 22042297, compound

HRID 1790881Notes

Reaction equation

HRID 1790881 reaction equation
[CH:1]([C:3]1([C:6]2([CH3:11])[O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1)=[CH2:2].B.[O:13]1CCCC1.[OH-].[Na+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[CH3:11][C:6]1([C:3]2([CH2:1][CH2:2][OH:13])[CH2:4][CH2:5]2)[O:7][CH2:8][CH2:9][O:10]1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 2723981Borane;tetrahydrofuranHCID 22042415HCID 22042415, compound

Product 1

HCID 22042297HCID 22042297, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.4 g of 8 is dissolved in 200 ml of tetrahydrofuran (THF), and 14 ml of borane-THF solution (1.0 M in THF) is added in drops at 0° C. under nitrogen. The reaction mixture is then allowed to reach room temperature, and it is stirred for 2 more hours. After cooling was again performed at 0° C., 17 ml of water, 17 ml of aqueous sodium hydroxide solution (25%) and 2 ml of hydrogen peroxide (30%) are added in succession and stirred for 1 more hour. Then, sodium thiosulfate solution is added, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.9 g of title compound 9 is obtained as a colorless oil.

Workup

  1. customto reach room temperature
  2. temperatureAfter cooling
  3. customwas again performed at 0° C.
  4. stirringstirred for 1 more hour
  5. extractionextracted with ethyl acetate
  6. washwashed with sodium chloride solution
  7. customdried on sodium sulfate
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-5f9a49c677524ef5847fd01a3d22ff13
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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