Hydrogen Peroxide → HCID 58677377, compound

HRID 747558Notes

Reaction equation

HRID 747558 reaction equation
[CH:1]([CH:3]1[O:7][CH:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)=[O:2].C(=O)([O-])[O-:18].[K+].[K+].OO>>[CH:1]([C:3]1[O:7][C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]([NH2:14])=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 85998175HCID 85998175, compound

Product 1

HCID 58677377HCID 58677377, compoundYield 33.1%

Procedure

Combine 4-(5-Formyl-tetrahydro-furan-2-yloxy)-benzonitrile (1.0 g, 4.69 mmol), dimethylsufoxide (100 mL), potassium carbonate (0.32 g, 2.35 mmol), and 1 mL of 30% hydrogen peroxide solution. Stir 18 hours at ambient temperature. Dilute with 300 mL of ice/water, extract with ethyl acetate (3×150 mL). Wash the organic phase with 100 mL of water, and 100 mL of brine. Dry the organic phase over sodium sulfate, filter, and concentrate under vacuum. Purify via ISCO™ 100 c system using a gradient of 75:25 hexane/ethyl acetate to 25:75 hexane/ethyl acetate as eluting solvent to give 0.18 g (18%) of the title compound: 1H NMR (DMSO-d6): 9.38 (s, 1H), 7.6 (d, 1H, J=3.8 Hz), 7.30-7.40 (m, 3H), 6.0 (d, 2H, J=3.7 Hz).

Workup

  1. extractionextract with ethyl acetate (3×150 mL)
  2. washWash the organic phase with 100 mL of water, and 100 mL of brine
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify via ISCO™ 100 c system
  7. washas eluting solvent

Sources & evidence

ORD record
ord-a48ad69eaa424833a124104a8d6d91b6
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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