HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-Ethynyl-1-(1-benzyloxycyclopropyl)-2-methyl-benzene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 4-iodobenzoate | HCID 142891 | — |
| Reactant | Methyl{4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-phenyl}-acetate | HCID 86585923 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | 4-Ethynyl-1-(1-benzyloxycyclopropyl)-2-methyl-benzene | HCID 22568852 | 54% |
Reaction Steps
Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-3-methyl-benzene (Intermediate 76, 90.0 mg, 0.34 mmol) and ethyl-4-iodo benzoate (Reagent A, 95.0 mg, 0.34 mmol) in triethylamine (6 mL) was treated with copper(I)iodide (23.0 mg, 0.12 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (80 mg, 0.11 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 68.0 mg (54%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06387892B1 |
| Source dataset | uspto-grants-2002_05 |
| ORD ID | ord-c7eb16dc7e0d4122b2771a2f7c0e915f |
| Source note | uspto-grants-2002_05 |