HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → [4-(1-Benzyloxycyclopropyl)-3-methyl-phenylethynyl]-trimethylsilane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-Bromo-1-(1-benzyloxycyclopropyl)-2-methyl-benzene | HCID 22568846 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | [4-(1-Benzyloxycyclopropyl)-3-methyl-phenylethynyl]-trimethylsilane | HCID 22568919 | 89.7% |
Reaction Steps
Using General Procedure D; 4-bromo-1-(1-benzyloxycyclopropyl)-2-methyl-benzene (Intermediate 74, 320.0 mg, 1.00 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (19.0 mg, 0.1 mmol) and then sparged with argon for 5 minutes. Trimethylsilylacetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (70.0 mg, 0.05 mmol). The resulting reaction mixture was heated to 70° C. for 5d. The title compound (300.0 mg, 89%) was isolated by chromatography (0-2% EtOAc—hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06855512B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-b9d4a0b285a840fa87b409396428e7fa |
| Source note | uspto-grants-2005_02 |