HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 1-(4-Pentylphenyl)ethynyl-3-triisopropylsiloxynaphthalene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-Ethynyl-4-pentylbenzene | HCID 2775131 | — |
| Reactant | 4-Bromo-2-triisopropylsiloxynaphthalene | HCID 67162464 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-(4-Pentylphenyl)ethynyl-3-triisopropylsiloxynaphthalene | HCID 67162368 | 33.1% |
Reaction Steps
A solution of 3-triisopropylsilyoxy-1-bromonaphthalene (2.32 g, 6.1 mmol), (4-pentylphenyl)acetylene (1.58 g, 9.2 mmol), Pd(PPh3)2Cl2 (129 mg, 3 mol %), PPh3 (240 mg, 15 mol %) and CuI (88 mg, 7.5 mol %) in Et3N (20 mL) under N2 was heated at reflux for 4 h. The resulting mixture was cooled, diluted with Et2O, filtered and the solvent removed under reduced pressure. The residue was chromatographed on silica using hexanes as eluent. The solvent was removed under reduced pressure to give the title compound (0.95 g, 33%) as a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08703978B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-26135af3f66d468e8ac5f8856bc1c2a3 |
| Source note | uspto-grants-2014_04 |