HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 2,2,2-Trifluoro-1-{5-[(trimethylsilyl)ethynyl]-2-thienyl}ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromothiophene | HCID 13851 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one | HCID 19971587 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2,2,2-Trifluoro-1-{5-[(trimethylsilyl)ethynyl]-2-thienyl}ethanone | HCID 68507078 | — |
Reaction Steps
A mixture of 5-bromo-thiophene Example 3, C2 (1.0 eq), Pd(PPh3)2Cl2 (0.025 eq), CuI (0.05 eq) and Et3N (28.7 eq) in THF (0.25 M) was degassed with a stream of Ar for 30 min. Trimethylsilylacetylene (1.5 eq) was added and the mixture was stirred O/N at RT. Evaporation of the solvent gave a residue which was purified by flash column chromatography on silica using 0-5% EtOAc/Petroleum ether to yield the desired compound as a yellow oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.83-7.78 (1H, m), 7.25 (1H, bs), 0.28 (9H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07799825B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-31f1ae1c8f914accaf5210aecfa5c8e3 |
| Source note | uspto-grants-2010_09 |