Hydrogen Peroxide → 3-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1-ol

HRID 479143Notes

Reaction equation

HRID 479143 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[O:7][C:8]=1[CH3:9])[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH-:27].[Na+].OO>O.C1COCC1>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:6]2[O:7][C:8]([CH3:9])=[C:4]([CH2:1][CH2:2][CH2:3][OH:27])[N:5]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 180034954-Allyl-2-(4-methoxy-phenyl)-5-methyl-oxazole

Product 1

HCID 180035253-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 4-allyl-2-(4-methoxy-phenyl)-5-methyl-oxazole (4.51 g, 19.7 mmol) was dissolved in 60 ml of abs. THF and and treated at 0° with 100 ml of 9-BBN-solution (0.5 M hexane). Hydroboration was allowed to proceed for 2 h at RT. Afterwards, 56 ml of 3N NaOH and 114.5 ml of 30% H2O2 was added simultaneously, whereby the internal temperature rose to 45°. After 1 h, the heterogeneous mixture was diluted with ice and water, extracted twice with AcOEt, washed water, and dried over natrium sulfate. Evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=1/3) yielded 4.54 g of the title compound as colorless oil.

Workup

  1. dissolutionwas dissolved in 60 ml of abs
  2. customrose to 45°
  3. waitAfter 1 h
  4. extractionextracted twice with AcOEt
  5. washwashed water
  6. dry with materialdried over natrium sulfate
  7. customEvaporation of the solvents

Sources & evidence

ORD record
ord-05f45f6bb3f7424eb6596ed46b0c91d4
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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