Hydrogen Peroxide → HCID 69649039, compound

HRID 1744769Notes

Reaction equation

HRID 1744769 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]2[C:4]=1[CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8]2.[OH-:16].[Na+].OO>O1CCCC1.C(OCC)(=O)C>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]2[C:9]=1[CH2:8][C@@H:7]([CH3:15])[C@H:6]([OH:16])[CH2:5]2

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22223280HCID 22223280, compound

Product 1

HCID 69649039HCID 69649039, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4 (5.00 g, 24.5 mmol) in tetrahydrofuran (100 ml) was cooled to 0° C. and treated with 1 M borane-tetrahydrofuran complex (24.5 mL, 24.5 mmol) and the resulting solution was stirred at room temperature for 4 h. Then, 12 mL of 3 N NaOH solution was added slowly to the stirring reaction solution followed by the addition of 6 mL of 30% aqueous hydrogen peroxide. After stirring for 30 min, the resultant mixture was diluted with 500 mL of ethyl acetate and washed by brine (2×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated, and the residue was purified on silica gel (30% ethyl acetate/hexane) to give 5 as a white solid.

Workup

  1. additiontreated with 1 M borane-tetrahydrofuran complex (24.5 mL, 24.5 mmol)
  2. stirringAfter stirring for 30 min
  3. washwashed by brine (2×100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-895a8b0f5aec44f284ca2ad928719c49
Source dataset
uspto-grants-2006_03
Patent number
US07018797B2

Reaction notes

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