HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-[2-(2,2,2-Trifluoro-1-hydroxy-ethyl)-phenyl]-pyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 5-(2-Formylphenyl)picolinonitrile | HCID 86621089 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-[2-(2,2,2-Trifluoro-1-hydroxy-ethyl)-phenyl]-pyridine-2-carbonitrile | HCID 66743510 | 95% |
Reaction Steps
Tetrabutylammonium fluoride (5.3 μl, 1.0 M solution in tetrahydrofuran) was added to a solution of 5-(2-formyl-phenyl)-pyridine-2-carbonitrile (110 mg, 0.53 mmol) and trifluoromethyltrimethylsilane (120 μl, 0.81 mmol) in 5 ml THF at 0° C. The formed mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The product was extracted with ethyl acetate (3×50 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 140 mg of 5-[2-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-pyridine-2-carbonitrile, yield 95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07553840B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-a1f492eaecd34fcfb11484d044589e8c |
| Source note | uspto-grants-2009_06 |