Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 59790342 | HCID 59790342 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 67539293 | HCID 67539293 | 70% |
Reaction Steps
A mixture of 1-(3-bromophenyl)-2-(4-(difluoromethoxy)phenyl)ethane-1,2-dione (0.500 g, 1.41 mmol), prop-2-yn-1-ol (0.395 g, 7.04 mmol), bis(triphenylphosphine)palladium(II) chloride (0.099 g, 0.14 mmol), copper(I) iodide (0.021 g, 0.11 mmol) and triethylamine (0.62 g, 6.11 mmol) in CH3CN (3 mL) was stirred at 60° C. overnight. The solvent is removed and the material is absorbed onto celite and purified by flash chromatography (silica, 25:75 ethyl acetate/hexanes) to afford 1-(4-(difluoromethoxy)phenyl)-2-(3-(3-hydroxyprop-1-ynyl)phenyl)ethane-1,2-dione (0.326 g, 70%) as an off white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07723368B2 |
|---|
| Source dataset | uspto-grants-2010_05 |
|---|
| ORD ID | ord-066c4bfe1fb048a08a529acc4ec16a39 |
|---|
| Source note | uspto-grants-2010_05 |
|---|
