HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1936152Generated: October 30, 2026
Trimethylsilylacetylene → 1-(2-Methyl-4-trimethylsilanylethynyl-benzyl)-1H-imidazole
https://huagongshe.com/reaction/1936152
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Ethylacetate methanol | HCID 21584119 | — |
| Reactant | 1-(4-Bromo-2-methyl-benzyl)-1H-imidazole | HCID 22568822 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-(2-Methyl-4-trimethylsilanylethynyl-benzyl)-1H-imidazole | HCID 22568964 | 82% |
Reaction Steps
Using General Procedure D; 1-(4-bromo-2-methyl-benzyl)-1H-imidazole (Intermediate 139, 160.0 mg, 0.64 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (12.0 mg, 0.07 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.70 g, 0.71 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (45.0 mg, 0.07 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (140.0 mg, 82%) was isolated by chromatography (5% MeOH-EtOAc ) as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06387951B1 |
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| Source dataset | uspto-grants-2002_05 |
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| ORD ID | ord-19626ce36eba416dae5d133b632b2f22 |
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| Source note | uspto-grants-2002_05 |
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