Potassium Iodide → HCID 67058166, compound

HRID 1515085Notes

Reaction equation

HRID 1515085 reaction equation
[CH2:1]([O:3][CH:4]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:3][CH:4]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:28][C:27]2[CH:30]=[CH:31][CH:32]=[C:25]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:26]=2)=[CH:15][CH:16]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 932913-Phenoxybenzyl chlorideHCID 67058135Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate

Product 1

HCID 67058166HCID 67058166, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) was dissolved in dimethylformamide (2.0 mL), and 3-phenoxybenzyl chloride (116 μL, 0.63 mmol), potassium carbonate (174 mg, 1.26 mmol), and potassium iodide (catalytic amount, about 5 mg) were sequentially added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 40° C. for 4 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride was added, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound was obtained (165 mg, yield: 93%).

Workup

  1. extractionthe organic matter was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution, then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  6. customwas obtained
  7. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound
  8. customwas obtained (165 mg, yield: 93%)

Sources & evidence

ORD record
ord-960fcc8218334b0aaa2dcced143857a3
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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