HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| Reactant | 4-(4,4,4-Trifluorobutoxy)benzaldehyde | HCID 53724788 | — |
| Catalyst | Cesium fluoride | HCID 25953 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2,2,2-Trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethanol | HCID 86685847 | 123.4% |
Reaction Steps
To the solution of Intermediate 2A (26.7 g, 114 mmol) and trimethyl(trifluoromethyl)silane (16.9 g, 119 mmol) in anhydrous DME (112 mL) was added CsF (500 mg, 3.29 mmol). The reaction was stirred at rt for 16 h. To the mixture was added 4 N aq HCl (114 mL) and the reaction was stirred at rt for 2.5 h. The reaction was diluted with EtOAc (300 mL) and washed with water, sat'd aq NaHCO3, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide Intermediate 2B (42.5 g, 122%) as an oil. The crude product was used without further purification. LCMS Anal. Calc'd for C12H12F6O2 302.21, found [M−H] 301.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08791091B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-990dedffbd184b71894588ed0b152300 |
| Source note | uspto-grants-2014_07 |