HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 1-(2-(4-Iodophenoxy)ethyl)pyrrolidine | HCID 21959166 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Piperidine | HCID 8082 | — |
| Product | 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine | HCID 67363455 | — |
Reaction Steps
Under a nitrogen atmosphere 7.0 mL (49.5 mmol) ethynyl-trimethyl-silane is slowly added to a mixture of 14.3 g (45 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine, 1.04 g (0.9 mmol) tetrakis-triphenylphosphane-palladium and 171 mg (0.4 mmol) CuI in 140 mL piperidine (exothermic reaction) and stirred for 30 minutes. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618132B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-f8d4ea79d767455ca8110c0dc05435f5 |
| Source note | uspto-grants-2013_12 |