HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl 4-iodobenzoate → Ethyl4-[4-(1-benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 4-iodobenzoate | HCID 142891 | — |
| Reactant | 1-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene | HCID 22568983 | — |
| 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 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 | US06531599B2 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-25060bc10d9344a4aeac19e6b938e08c |
| Source note | uspto-grants-2003_03 |