(E)-1-(2-hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one → 8-nitro-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one

HRID 876526Notes

Reaction equation

HRID 876526 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:24])/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21]>CS(C)=O.O1CCOCC1>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:2]=1[O:1][C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:21])([F:22])[F:23])=[CH:12][C:11]2=[O:24])([O-:10])=[O:9]

Participants

3

Reactant 1

HCID 58477301(E)-1-(2-hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one

Product 1

HCID 584772298-nitro-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-oneYield 92.3%

Reagents, catalysts & solvents 1

HCID 22724500DMSO dioxaneSolvent

Procedure

A solution of (E)-1-(2-hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one 9 (1.4 g, 4.2 mmol) and SeO2 (1.4 g, 12.5 mmol) in DMSO/dioxane (35 ml, 1:15) was heated at reflux for 12 h. After cooling to room temperature, the reaction mixture was passed through a filter and the filtrate was concentrated to dryness. The crude residue was suspended in H2O and collected by filtration to give 10 as a yellow solid (1.3 g, 92% yield).

Workup

  1. temperatureat reflux for 12 h
  2. filtrationa filter
  3. concentrationthe filtrate was concentrated to dryness
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e51a187cef5644b888090a0aa37ecbd5
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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