HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 59164393, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-Iodo-6-methoxynicotinaldehyde | HCID 45480325 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59164393 | HCID 59164393 | 68% |
Reaction Steps
4-Iodo-6-methoxynicotinaldehyde (0.41 g, 1.6 mmoles), trimethylsilylacetylene (0.35 mL, 2.8 mmol), PdCl2(PPh3)2 (catalytic amount), CuI (catalytic amount), triethylamine (2 mL) and THF (10 mL) were stirred at 60° C. for 2 h. The volatiles were evaporated and the residue was taken up in water and extracted with ether. The organic phase was dried, filtered and concentrated. Purification by column chromatography with EtOAc-heptanes (1:3) as eluent gave 0.25 g (68% yield) of 6-methoxy-4-[(trimethylsilyl)ethynyl]nicotinaldehyde.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07655664B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-b93e2bc2ab644cb5a9e1ebf9d3b4e6a4 |
| Source note | uspto-grants-2010_02 |