Hydrogen Peroxide → HCID 69146728, compound

HRID 2223845Notes

Reaction equation

HRID 2223845 reaction equation
[CH2:1]([C:4]1([CH2:10][O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[OH2:19].[OH-].[Na+].OO>O1CCCC1>[CH2:13]([Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[O:11][CH2:10][C:4]1([CH2:1][CH2:2][CH2:3][OH:19])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[CH3:14]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 14798Sodium HydroxideHCID 23021184HCID 23021184, compound

Product 1

HCID 69146728HCID 69146728, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [1-(allylcyclohexyl)methoxy]triethylsilane (1.70 g) in tetrahydrofuran (35 mL) were added a 2M borane-methyl sulfide complex solution in tetrahydrofuran (6.48 mL, 12.96 mmol) under ice cooling. The solution was stirred under ice cooling for 2 hours. To this were then added water, a 3N aqueous sodium hydroxide solution (6.5 mL) and 30% hydrogen peroxide (6.5 mL). The solution was stirred at room temperature for 16 hours. Water was added and the solution was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=7:3) to give the title compound (810 mg).

Workup

  1. stirringThe solution was stirred at room temperature for 16 hours
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed in turn with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-ae76d46f4d054d37915aa6b83afcd56a
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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