HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2-(5-Pyrimidinyl)-α-(trifluoromethyl)benzenemethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | 2-(pyrimidin-5-yl)benzaldehyde | HCID 3807860 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(5-Pyrimidinyl)-α-(trifluoromethyl)benzenemethanol | HCID 66743537 | 84% |
Reaction Steps
Tetrabutylammonium fluoride (TBAF, 0.1 ml of 1M in THF) was added to a solution of 2-pyrimidin-5-yl-benzaldehyde (184 mg, 1 mmol) and trifluoromethyl trimethylsilane (TMSCF3, 0.2 ml, 1.2 mmol) in 10 ml THF at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The mixture was then treated with 3 ml of 1M HCl and stirred overnight. The product was extracted with ethyl acetate (3×20 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 0.21 g of 2,2,2-trifluoro-1-(2-pyrimidin-5-yl-phenyl)-ethanol (yield: 84%), which was directly used in next step without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07709493B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-822843af2614406a93bf5b2a24716e10 |
| Source note | uspto-grants-2010_05 |