HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-[1,1-Dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Iodopyridine | HCID 221126 | — |
| Reactant | 4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile | HCID 2779072 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 4-[1,1-Dimethyl-3-(2-pyridyl)-2-propynyloxy]benzonitrile | HCID 15732962 | 88.2% |
Reaction Steps
53 mg of copper(I) iodide, 293 mg of triphenylphosphine and 99 mg of palladium(II) chloride were dissolved in 320 ml of diethylamine. 10.4 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile and 11.5 g of 2-iodopyridine were added and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 days. Water and ethyl acetate were added and the organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and then ethyl acetate/petroleum ether (1:2) for the elution to give 12.98 g of 4-[1,1-dimethyl 3-(2-pyridyl)-2-propynyloxy] benzonitrile in the form of an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05118694 |
| Source dataset | uspto-grants-1992_06 |
| ORD ID | ord-5079b574a60741b4af90bbfcbb4d42a0 |
| Source note | uspto-grants-1992_06 |