Hydrogen Peroxide → HCID 86653780, compound

HRID 1021207Notes

Reaction equation

HRID 1021207 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH:28]=[CH2:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B1C2CCCC1CCC2.[OH-].[Na+].OO.C(OC(C)C)(=[O:45])C>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28][CH2:29][OH:45])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 7915Isopropyl AcetateHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86653779HCID 86653779, compound

Product 1

HCID 86653780HCID 86653780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-3-butene (1.1 g, 2.85 mmol) in THF (15 mL) was treated with 9-BBN (560 mg, 4.27 mmol, 1.5 equiv.) at room temperature. After 2.5 h the clear colorless solution was treated with 2.5 M aqueous NaOH (6 mL, 15 mmol), was added followed by slow, dropwise addition of 35% w/w H2O2 (5 mL, 58.5 mmol). During addition, the internal reaction temperature was kept below 35° C. by ice bath immersion. The biphasic solution was stirred for 1.5 h at room temperature, 35 mL isopropyl acetate added and the layers separated. The aqueous phase was extracted 3×25 mL isopropyl acetate and the combined organics washed 2×25 mL saturated aqueous NaCl and dried over Na2SO4. Flash chromatography (gradient elution 10-60% EtOAc/heptane) yielded 741 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butan-1-ol as a clear colorless oil. M++H at 405 m/z;

Workup

  1. additionwas added
  2. additionDuring addition
  3. customthe internal reaction temperature was kept below 35° C. by ice bath
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted 3×25 mL isopropyl acetate
  6. washthe combined organics washed 2×25 mL saturated aqueous NaCl
  7. dry with materialdried over Na2SO4
  8. washFlash chromatography (gradient elution 10-60% EtOAc/heptane)

Sources & evidence

ORD record
ord-bc594d0ffbfe4cc99ae22f69734cb196
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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