Hydrogen Peroxide → HCID 21949661, compound

HRID 2215250Notes

Reaction equation

HRID 2215250 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:7][C:8]=1[CH2:9][CH3:10])[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH:24]O.[OH-].[Na+]>CCOC(C)=O.O.C1COCC1>[C:11]([C:6]1[O:7][C:8]([CH2:9][CH3:10])=[C:4]([CH2:1][CH2:2][CH2:3][OH:24])[N:5]=1)([CH3:13])([CH3:12])[CH3:14]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 21949625HCID 21949625, compound

Product 1

HCID 21949661HCID 21949661, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.693 g of 4-allyl-2-tert-butyl-5-ethyl-oxazole (3.585 mmol) was dissolved under an argon atmosphere in 10 ml of abs. THF and treated at 0° with 3 eq. of 9-BBN (0.5 M, hexane). After 3 h at ambient temperature, when TLC indicated the absence of starting material, 20.9 ml of 30% H2O2 and 10. 3 ml of 3N NaOH was added dropwise, but simultaneously. After cessation of the strongly exothermic reaction, the mixture was diluted with AcOEt and water, the layers separated, the aqueous phase reextracted with AcOEt, and the combined organic phases washed with water. Drying over sodium sulfate and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=1/1) afforded 0.400 g of 3-(2-tert-butyl-5-ethyl-oxazol-4-yl)-propan-1-ol as colorless oil.

Workup

  1. customAfter cessation of the strongly exothermic reaction
  2. customthe layers separated
  3. washthe combined organic phases washed with water
  4. dry with materialDrying over sodium sulfate and evaporation of the solvents

Sources & evidence

ORD record
ord-04c55471c3bb4815920e8bac93e5eff2
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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