Water → HCID 20795053, compound

HRID 1070575Notes

Reaction equation

HRID 1070575 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([NH:17]C(=O)C(F)(F)F)[C:9]=2[CH:24]=[CH:25][CH3:26])=[O:5])[CH3:2].[Se](=O)=O.O>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]1[C:9]=2[CH:24]=[CH:25][CH:26]=[N:17]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium Dioxide2×HCID 73710678HCID 73710678, compound

Product 1

HCID 20795053HCID 20795053, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4-oxo-8-propenyl-7-(2,2,2-trifluoro-acetylamino)-4H-chromene-2-carboxylic acid ethyl ester (3.7 g, 10 mmole) in 100 mL of dioxan was added 4.4 g (40 mmole) of selenium dioxide. The mixture was refluxed under nitrogen for 5 hours. An additional 1.0 g of selenium dioxide was added and reflux continued for 8 hours. After the reaction had cooled, 500 mL of water was added and the mixture was extracted with first 300 mL and then 200 mL of ethyl acetate. The combined organic extracts were washed with water and with saturated brine, dried over sodium sulfate, filtered and evaporated in vacuum to give 2.0 g of the title compound as a yellow solid. An analytically pure sample of yellow solid (m.p. 146-147° C.) was obtained by column chromatography on silica gel with 0-5% ethyl acetate/methylene chloride as eluant.

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 5 hours
  2. temperaturereflux
  3. temperatureAfter the reaction had cooled
  4. extractionthe mixture was extracted with first 300 mL
  5. washThe combined organic extracts were washed with water and with saturated brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuum

Sources & evidence

ORD record
ord-c81700f60ab34b919b2829f0a008194d
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

Loading…