HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl alcohol → 3-(Pyridin-2-yl)prop-2-yn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | 2-Bromopyridine | HCID 7973 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 3-(Pyridin-2-yl)prop-2-yn-1-ol | HCID 3481147 | 77% |
Reaction Steps
The mixture that consists of 16.6 ml (173 mmol) of 2-bromopyridine, 21.6 ml of propargyl alcohol, 2.5 g of palladium-bis-triphenylphosphine-dichloride and 173 mg of copper(I) iodide is mixed with 510 ml of diethylamine and heated for 1.5 hours to 80° C. After filtration and removal of the solvent, the residue is purified by chromatography on fine silica gel with a gradient system that consists of n-hexane and ethyl acetate. 17.8 g (134 mmol, 77%) of the title compound is isolated as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06610736B1 |
| Source dataset | uspto-grants-2003_08 |
| ORD ID | ord-d28451f836ab49a793ad3f43adaff925 |
| Source note | uspto-grants-2003_08 |