HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → HCID 72212432, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 5-Bromo-3-pyridinecarboxaldehyde | HCID 2784734 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 72212432 | HCID 72212432 | — |
Reaction Steps
To a stirred solution of 5-bromonicotinaldehyde (1 g) and ethynyltrimethylsilane (792 mg) in Et3N (15 ml) was added tetrakis(triphenylphosphine)palladium (124 mg) and copper(I) iodide (51 mg). After 4 hours, the resulting mixture was filtrated and evaporated. The residue was dissolved in EtOAc and washed successively with dil. NH3aq, water and brine. The organic layer was dried over MgSO4 and evaporated. The residue was purified with silica gel column chromatography to give 5-[(trimethylsilyl)ethynyl]nicotinaldehyde as a slightly yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07459451B2 |
| Source dataset | uspto-grants-2008_12 |
| ORD ID | ord-b02b808dbca9444a91d6e7bcac2edc46 |
| Source note | uspto-grants-2008_12 |