Hydrogen Peroxide → 2,3-Epoxychromone

HRID 1940007Notes

Reaction equation

HRID 1940007 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[OH:12]O>CCOCC>[O:12]1[C:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:1][C:2]1=2

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 10286Chromone

Product 1

HCID 214655662,3-EpoxychromoneYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Chromone (3 g) was dissolved in ether (200 ml) and the solution was cooled to 0° C. in ice water. Then, 30% hydrogen peroxide (15 ml) and Triton B (10 ml) solution were added portionwise. The whole was stirred at 0° C. for 4 hours. After adding ice water, the reaction liquor was extracted with dichloromethane. The organic layer was washed with sodium thiosulfate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was fractionatedby silica gel column chromatography (diethyl ether/hexane =1:8) to give the titled compound (2.34 g; yield =75%). Melting point: 66°-67° C. Mass spectrum (M+): 162. 1H-NMR(CDCl3, δ ppm): 3.69 (d, 1H, H3), 5.67 (d, 1H, H2), 7.05 (d, 1H, H8), 7.14 (t, 1H, H6), 7.54 (t, 1H, H7), 7.79 (dd, 1H, H5).

Workup

  1. extractionthe reaction liquor was extracted with dichloromethane
  2. washThe organic layer was washed with sodium thiosulfate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-356d6a7794d84949845b5a6a9c170b34
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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