HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropylacetylene → HCID 57804112, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropylacetylene | HCID 138823 | — |
| Reactant | HCID 57804164 | HCID 57804164 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 57804112 | HCID 57804112 | 61% |
Reaction Steps
Ethyl 4-bromo-3-(cyclopropylmethoxy)benzoate (0.77 g, 2.57 mmol), ethynylcyclopropane (0.45 mL of a 70% w/v solution in toluene, 3.86 mmol), copper(I) iodide (49 mg, 0.26 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.36 g, 0.51 mmol) were placed in 50 mL triethylamine and stirred in a sealed tube at room temperature for 20 h. The reaction was diluted with MeOH and filtered through Celite®., then the filtrate was concentrated to an oil. Purification by column chromatography on silica gel using 25% EtOAc/hexane gave the product (0.47 g, 61%) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576099B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-77f1f828eb92436b9b1d44ead980cd40 |
| Source note | uspto-grants-2009_08 |