HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 4-Iodophenylacetate → Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 4-Iodophenylacetate | HCID 10378700 | — |
| 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 | Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate | HCID 86585923 | 161.4% |
Reaction Steps
Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-benzene (Intermediate 71, 60.0 mg, 0.20 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 66.0 mg, 0.24 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (15.0 mg, 0.08 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (56 mg, 0.08 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-7% EtOAc-hexanes) afforded 64.0 mg (81%) of the title compound as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06369261B1 |
| Source dataset | uspto-grants-2002_04 |
| ORD ID | ord-1271d850fa374d7a8a3a82628232b28f |
| Source note | uspto-grants-2002_04 |