HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 51796Generated: October 30, 2026
Trimethylsilylacetylene → 2-Methyl-4-trimethylsilanylethynyl-1-trimethlsilanyloxymethyl-benzene
https://huagongshe.com/reaction/51796
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | (4-Bromo-2-methyl-benzyloxy)-trimethylsilane | HCID 22568853 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 2-Methyl-4-trimethylsilanylethynyl-1-trimethlsilanyloxymethyl-benzene | HCID 22568863 | 65.1% |
Reaction Steps
Using General Procedure D; (4-bromo-2-methyl-benzyloxy)-trimethylsilane (Intermediate 134, 550.0 mg, 2.01 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (38.0 mg, 0.20 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (1.05 g, 10.6 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (142.0 mg, 0.20 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (380.0 mg, 65%) was isolated by chromatography (0-2% EtOAc-hexanes) as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06713647B2 |
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| Source dataset | uspto-grants-2004_03 |
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| ORD ID | ord-028ed70db1714b838868c3b3f58cbb84 |
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| Source note | uspto-grants-2004_03 |
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