Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | Potassium trimethylsilanolate | HCID 23668039 | — |
| Reactant | HCID 71239543 | HCID 71239543 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 89704694 | HCID 89704694 | — |
Reaction Steps
To a solution of 2,4-dichloro-6-trifluoromethylphenylacetic acid (0.36 mmol) in 3 mL toluene were added Et3N (0.44 mmol) and DPPA (0.36 mmol). The reaction mixture was heated to 110° C. for 3 h, cooled to 0° C. and a solution of potassium trimethylsilanolate (0.73 mmol, 1M in THF) was added. After stirring at RT for 30 min, an aqueous solution of 10% citric acid was added and the mixture was extracted twice with Et2O. The aqueous phase was basified with 1M NaOH solution and extracted 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409917B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-cd512eb600d84e62b94ed65a81c22abc |
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| Source note | uspto-grants-2016_08 |
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