HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-(4-Hydroxymethylphenylethynyl)benzylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-Iodobenzylamine | HCID 2737533 | — |
| Reactant | (4-Ethynylphenyl)methanol | HCID 11170993 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(4-Hydroxymethylphenylethynyl)benzylamine | HCID 67436539 | — |
Reaction Steps
A mixture of 4-iodo-(aminomethyl)-benzene (7.4 mmol), palladium acetate (0.015 mmol), triphenylphosphine (0.18 mmol), and CuI (0.18 mmol) in anhydrous THF (40 mL) is thoroughly degassed by purging under Ar. To this solution under Ar is added 4-hydroxymethylphenylacetylene (7.4 mmol) and Et3N (11 mmol). The mixture was then incubated at RT with stirring overnight. The mixture is diluted with EtOAc (150 mL) and the solids are removed by filtration through Celite. The crude residue obtained from the filtrate is purified by flash column chromatography (silica, 1:1 hexane:Et2O) to give the product as a slightly yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08034563B1 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-7b19e1b238c547819bf26007f017f348 |
| Source note | uspto-grants-2011_10 |