Dimethyl Sulfoxide → 7-(2-{2-[3-Fluoro-5-(trifluoromethyl)phenyl] (1,3-oxazol-5-yl)}ethoxy)-3-(4-hydroxyphenyl)chromen-4-one

HRID 1694656Notes

Reaction equation

HRID 1694656 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][C:11]([OH:17])=[CH:12][CH:13]=3)[O:8][CH:7]=2)=[CH:4][CH:3]=1.[F:20][C:21]1[CH:22]=[C:23]([C:36]([F:39])([F:38])[F:37])[CH:24]=[C:25]([C:27]2OC=[C:30]([CH2:32][CH2:33][CH2:34]I)[N:31]=2)[CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O.[OH2:50]>>[F:20][C:21]1[CH:26]=[C:25]([C:27]2[O:50][C:32]([CH2:33][CH2:34][O:17][C:11]3[CH:10]=[C:9]4[C:14]([C:15](=[O:16])[C:6]([C:5]5[CH:18]=[CH:19][C:2]([OH:1])=[CH:3][CH:4]=5)=[CH:7][O:8]4)=[CH:13][CH:12]=3)=[CH:30][N:31]=2)[CH:24]=[C:23]([C:36]([F:38])([F:39])[F:37])[CH:22]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 10796Cesium carbonateHCID 5281708DaidzeinHCID 672790242-[5-Fluoro-3-(trifluoromethyl)phenyl]-4-(3-iodopropyl)-1,3-oxazole

Product 1

HCID 249606237-(2-{2-[3-Fluoro-5-(trifluoromethyl)phenyl] (1,3-oxazol-5-yl)}ethoxy)-3-(4-hydroxyphenyl)chromen-4-oneYield 76%

Procedure

4′,7-Dihydroxyisoflavone (31.3 mg, 0.123 mmol), 2-[5-fluoro-3-(trifluoromethyl)phenyl]-4-(3-iodopropyl)-1,3-oxazole (48.9 mg, 0.123 mmol, 1.0 equiv.) and cesium carbonate (40.0 mg, 0.123 mmol, 1.0 equiv) were placed in a 25 mL flask. To the flask was added dimethylsulfoxide (3 mL) at room temperature to dissolve the starting materials, and the reaction mixture stirred room temperature for 15 hours. To the mixture were added water (30 mL) and the whole was extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with brine (30 mL) and dried with sodium sulfate to give a crude mixture as colorless oil (64.2 mg). The crude mixture was purified by column-chromatography (SiO2=80 g, hexane/EtOAc=2:1 to 1:1) to give 7-(2-{2-[3-fluoro-5-(trifluoromethyl)phenyl](1,3-oxazol-5-yl)}ethoxy)-3-(4-hydroxyphenyl)chromen-4-one (49.1 mg, 0.0934 mmol, 76%) as colorless crystals. Similarly prepared was 7-(3-{2-[3-fluoro-5-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}propoxy)-3-(4-hydroxyphenyl)chromen-4-one.

Workup

  1. dissolutionto dissolve the starting materials
  2. extractionthe whole was extracted with ethyl acetate (30 mL×3)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried with sodium sulfate
  5. customto give a crude mixture as colorless oil (64.2 mg)
  6. customThe crude mixture was purified by column-chromatography (SiO2=80 g, hexane/EtOAc=2:1 to 1:1)

Sources & evidence

ORD record
ord-d981441b39e34f67868eccb043a1931c
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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