Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triisopropylsilyl chloride | HCID 139400 | — |
| Reactant | 1-[4-(Trifluoromethyl)phenyl]ethane-1,2-diol | HCID 11481148 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67402674 | HCID 67402674 | 82.1% |
Reaction Steps
1-(1,2-Dihydroxyethyl)-4-(trifluoromethyl)benzene (81.0 mg, 0.393 mmol) and triethylamine (57.6 μL, 0.413 mmol) were dissolved in N,N-dimethylformamide (1.6 mL). To this, triisopropylsilyl chloride (87.2 μL, 0.413 mmol) was added under a nitrogen atmosphere at 0° C. and the mixture was stirred at room temperature for 2 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give 1-(1-hydroxy-2-triisopropylsiloxyethyl)-4-(trifluoromethyl)benzene (Compound CM) (117 mg, yield: 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08673908B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-e8c0b778a5f8460d86a3469caca49f8e |
|---|
| Source note | uspto-grants-2014_03 |
|---|