Hydrogen Peroxide → HCID 86713809, compound

HRID 521860Notes

Reaction equation

HRID 521860 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:13][CH2:12][CH:11]=[CH:10][O:9][CH2:8]2)=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=[N:3]1.[OH-:17].[Na+].OO>C1COCC1>[CH3:1][N:2]1[C:6]([CH:7]2[CH2:8][O:9][CH2:10][CH:11]([OH:17])[CH2:12][CH2:13]2)=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86713808HCID 86713808, compound

Product 1

HCID 86713809HCID 86713809, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Borane dimethyl sulfide complex (2.0 mol/L) in THF (0.91 mL, 1.82 mmol) was added to a solution of 1-methyl-4-nitro-5-(2,3,4,5-tetrahydrooxepin-3-yl)pyrazole (204 mg, 0.91 mmol) in anhydrous THF (8 mL) at 0° C. The mixture was stirred at 0° C. for 15 min then warm to RT for 2 h. 1M NaOH (1.5 mL) and hydrogen peroxide (30 mass % in water) (0.8 mL) were added and the mixture was stirred at RT for 2 h. The reaction was quenched with water and extracted with DCM (2×) and EA (1×). Combined organic layers were washed with brine (10 ml) and concentrated to dryness. The residue was purified via silica gel chromatography (0-100% EtOAc/heptane) to afford 6-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-ol (53 mg, 24%).

Workup

  1. temperaturethen warm to RT for 2 h
  2. stirringthe mixture was stirred at RT for 2 h
  3. customThe reaction was quenched with water
  4. extractionextracted with DCM (2×) and EA (1×)
  5. washCombined organic layers were washed with brine (10 ml)
  6. concentrationconcentrated to dryness
  7. customThe residue was purified via silica gel chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-3f7b1621f0084c33975a93613d75e447
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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