HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Ethyl4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 4-iodobenzoate | HCID 142891 | — |
| Reactant | 4-Ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene | HCID 22568997 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | Ethyl4-[4-(1-isopropoxycyclopropyl)-3-methyl-phenylethynyl]-benzoate | HCID 22568844 | 56% |
Reaction Steps
Using General Procedure F; 4-ethynyl-1-(1-isopropoxycyclopropyl)-3-methyl-benzene (Intermediate 81, 80.0 mg, 0.13 mmol) and ethyl-4-iodo benzoate (Reagent A, 100.0 mg, 0.36 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (25.0 mg, 0.13 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)-palladium(II) (91 mg, 0.13 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 75.0 mg (56%) of the title compound as an orange solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06303785B1 |
| Source dataset | uspto-grants-2001_10 |
| ORD ID | ord-6a957a20d7874d9fa7b1e04f2e0333ed |
| Source note | uspto-grants-2001_10 |