HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → [3-(2-Methoxy-1,1-dimethyl-ethyl)-phenylethynyl]-trimethyl-silane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 2-(3-Bromophenyl)-2-methylpropyl methyl ether | HCID 67191411 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile triethylamine | HCID 21895542 | — |
| Product | [3-(2-Methoxy-1,1-dimethyl-ethyl)-phenylethynyl]-trimethyl-silane | HCID 67187907 | 89% |
Reaction Steps
To a solution of 1-bromo-3-(2-methoxy-1,1-dimethyl-ethyl)-benzene (1.62 g, 6.69 mmol) and trimethylsilylacetylene (1.2 mL, 8.7 mmol, 1.3 eq.) in MeCN-Et3N (50 mL, 7:3) was added Pd(PPh3)2Cl2 (0.23 g, 0.33 mmol. 0.05 eq.), CuI (0.038 g, 0.2 mmol, 0.03 eq.) and the mixture refluxed for 16 h. After cooling to ambient temperature and concentration under reduced pressure the residue was chromatographed (EtOAc-hexane, 2:98) to obtain 1.54 g (89%) of the desired product. NMR (DMSO-d6): 7.28-7.00 (m, 4H), 3.16 (s, 2H), 2.98 (s, 3H), 1.00 (s, 6H), 0.1 (s, 9H). MS (DCI): 261 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07375126B2 |
| Source dataset | uspto-grants-2008_05 |
| ORD ID | ord-5769c9bba7e5498c88a42d9a99bb9ab8 |
| Source note | uspto-grants-2008_05 |