HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (3-tert-Butyl-phenylethynyl)-trimethyl-silane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | HCID 22261847 | HCID 22261847 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | (3-tert-Butyl-phenylethynyl)-trimethyl-silane | HCID 14989665 | — |
Reaction Steps
Following General Procedure D and using trifluoromethanesulfonic acid, 3-tert-butyl-phenyl ester (Intermediate 101, 2.54 g, 9.0 mmol), triethyl amine (2 mL), copper(I)iodide (0.63 g, 3.33 mmol), trimethylsilyl acetylene (5 mL, 36 mmol) and dichlorobis(triphenylphosphine)palladium(II) (1.6 g, 2.25 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound was obtained as a brown oil that was used as such for the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07468391B2 |
| Source dataset | uspto-grants-2008_12 |
| ORD ID | ord-aef41e2c081648ef8d7dc38b753f3f66 |
| Source note | uspto-grants-2008_12 |