HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl 4-iodobenzoate → Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 4-iodobenzoate | HCID 142891 | — |
| Reactant | Ethyl4-[4-(1-isopropoxycyclopropyl)-phenylethynyl]-benzoate | HCID 22568976 | — |
| 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)-phenylethynyl]-benzoate | HCID 22568905 | 91% |
Reaction Steps
Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-benzene (Intermediate 71, 60.0 mg, 0.24 mmol) and ethyl-4-iodo benzoate (Reagent A, 72.0 mg, 0.26 mmol) in triethylamine (4 mL) was treated with copper(I)iodide (17.0 mg, 0.09 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (61 mg, 0.09 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc—hexanes) afforded 85.0 mg (91%) of the title compound as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06855512B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-867652077ff241399f602148dffaa87f |
| Source note | uspto-grants-2005_02 |