HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 1-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one | HCID 45480353 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone | HCID 67430140 | — |
Reaction Steps
Trimethylsilylacetylene (16 ml) is added to a solution of 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (16.9 q, example 1, step A), Pd(PPh3)2Cl2 (3.78 g), CuI (1.46 g) and triethylamine (16 ml) in DMF (15 ml). After 3 hours at room temperature, the reaction is quenched with water and extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by filtration over a plug of silica gel eluting with dichloromethane to yield 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) as yellow solid. The compound is used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08383659B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-47a109eae293408b818b08e6b8721a45 |
| Source note | uspto-grants-2013_02 |