Hydrogen Peroxide → HCID 58377413, compound

HRID 2068668Notes

Reaction equation

HRID 2068668 reaction equation
[CH2:1]([C:6]1([CH:12]=[CH2:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[OH:34]O.[OH-].[Na+]>C1COCC1.O>[CH2:1]([C:6]1([CH2:12][CH2:13][OH:34])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 54264658HCID 54264658, compound

Product 1

HCID 58377413HCID 58377413, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-5 (90 mg, 0.50 mmol) in THF (3.4 mL) was added to a solution of 9-BBN dimer (206 mg, 0.84 mmol) in THF (3 mL). The reaction was placed in a 60° C. oil bath and after 2.5 h, a solution of H2O2 (35%, 1.4 mL)/NaOH (0.5 M, 1.4 mL)/H2O (0.35 mL) was added. The reaction was heated to reflux for 1 h and then allowed to cool to room temperature. H2O (20 mL) was added and the mixture was extracted with ethyl acetate (3×25 mL). The combined ethyl acetate solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography using a Combiflash system by Teledyne Isco (4 g silica gel, 0→30% ethyl acetate/hexanes) which gave the title compound (70 mg, 71%).

Workup

  1. customwas placed in a 60° C.
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 1 h
  4. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  5. washThe combined ethyl acetate solution was washed with brine
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-90aa92cf6c7b4ee98048d6078cdf6201
Source dataset
uspto-grants-2012_10
Patent number
US08299068B2

Reaction notes

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