Sodium Iodide → HCID 42605467, compound

HRID 1694646Notes

Reaction equation

HRID 1694646 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.Cl[CH2:21][C:22]1[N:23]=[C:24]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=2)[O:25][CH:26]=1.[I-].[Na+].[OH-].[K+]>O.CS(C)=O>[F:33][C:31]1[CH:30]=[C:29]([C:34]([F:35])([F:36])[F:37])[CH:28]=[C:27]([C:24]2[O:25][CH:26]=[C:22]([CH2:21][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)[N:23]=2)[CH:32]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 5281708DaidzeinHCID 67279270HCID 67279270, compound

Product 1

HCID 42605467HCID 42605467, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4′,7-Dihydroxyisoflavone (101.7 mg, 0.40 mmol), 4-(chloromethyl)-2-[5-fluoro-3-(trifluoromethyl)phenyl]-1,3-oxazole, prepared as described in Example 1 (111.8 mg, 040 mmol, 1.0 equiv.), sodium iodide (59.6 mg, 0.40 mmol, 1.0 equiv), and potassium hydroxide powder (22.4 mg, 0.4 mmol, 1.0 equiv) were placed in a 25 mL flask equipped with a condenser. To the flask was added dimethylsulfoxide (3 mL) at room temperature under nitrogen. The solution was heated at 60° C. for 1 hour. 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 Na2SO4, to give a crude mixture as colorless oil (204.7 mg). The crude mixture was purified by column-chromatography (silica gel=25 g, eluting with hexane/ethyl acetate=7:1) to give crude product (149.3 mg) as colorless crystals. Recrystallization of this crude product gave 7-({2-[5-fluoro-3-(trifluoromethyl)phenyl]-(1,3-oxazol-4-yl)}methoxy)-3-(4-hydroxyphenyl)chromen-4-one as a colorless powder.

Workup

  1. customwere placed in a 25 mL flask
  2. customequipped with a condenser
  3. extractionthe whole was extracted with ethyl acetate (30 mL×3)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried with Na2SO4
  6. customto give a crude mixture as colorless oil (204.7 mg)
  7. customThe crude mixture was purified by column-chromatography (silica gel=25 g, eluting with hexane/ethyl acetate=7:1)
  8. customto give crude product (149.3 mg) as colorless crystals
  9. customRecrystallization of this crude product

Sources & evidence

ORD record
ord-166eec63360447bab600a161ace5b9c7
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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