Potassium Iodide → 6-methoxy-7-(oxiranylmethoxy)-2H-1-benzopyran-2-one

HRID 22357

Reaction equation

HRID 22357 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:6]2=[CH:7][C:8]=1[OH:9].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:15][CH:17]2[CH2:18][O:19]2)=[CH:7][C:6]2[O:10][C:11](=[O:12])[CH:13]=[CH:14][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 5280460Scopoletin

Product 1

HCID 199277176-methoxy-7-(oxiranylmethoxy)-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.0 g (130 mmol) of scopoletine, 15.3 ml (196 mmol) epichlorohydrin, 36.0 g (260 mmol) potassium carbonate and 2.5 g of potassium iodide are agitated in 500 ml DMF under nitrogen for 3 h at 80° C. After vacuum evaporation and repeated extraction with hot ethanol re-evaporation was performed. 21.2 g (66%); fusion point 143°-145° C. (from ethanol).

Workup

  1. customAfter vacuum evaporation
  2. extractionextraction
  3. customwith hot ethanol re-evaporation
  4. customfusion point 143°-145° C. (from ethanol)

Sources & evidence

ORD record
ord-0fed15fd2091475685652c7edc9bf58e
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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