HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene → Ethyl4-[4-(1-benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene | HCID 22568983 | — |
| Reactant | Ethyl-4-iodo-benzoate benzoate | HCID 69887287 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Ethyl4-[4-(1-benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate | HCID 22568992 | 72% |
Reaction Steps
Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene (Intermediate 90, 90.0 mg, 0.33 mmol) and ethyl-4-iodo benzoate (Reagent A, 100.0 mg, 0.36 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (21.0 mg, 0.11 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (77 mg, 0.11 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 100.0 mg (72%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06713647B2 |
| Source dataset | uspto-grants-2004_03 |
| ORD ID | ord-1b781f55accc43c9b1b27ad6a6104566 |
| Source note | uspto-grants-2004_03 |