Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 3-Phenoxybenzyl chloride | HCID 93291 | — |
| Reactant | Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate | HCID 67058135 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67058166 | HCID 67058166 | 93% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08222281B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-960fcc8218334b0aaa2dcced143857a3 |
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| Source note | uspto-grants-2012_07 |
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