HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Undecyn-3-ol → 5-(6-[(3RS)-3-hydroxy-1-undecinyl]-2-pyridyl-methyl}-tetrahydrofuran-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Undecyn-3-ol | HCID 247766 | — |
| Reactant | 5-[(6-Bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one | HCID 19966491 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 5-(6-[(3RS)-3-hydroxy-1-undecinyl]-2-pyridyl-methyl}-tetrahydrofuran-2-one | HCID 131719078 | 43.8% |
Reaction Steps
A solution of 500 mg of 5-[(6-bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one in 13 ml of triethylamine and 2 ml of tetrahydrofuran is mixed with 350 mg of (3RS)-1-undecin-3-ol, 37 mg of bis-(triphenylphosphine)-palladium(II) chloride and 5 mg of copper(I) iodide and the mixture is stirred for 3 days at room temperature. The reaction mixture is evaporated to dryness, distributed between water and ethyl acetate, dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-35% ethyl acetate. 294 mg of 5-(6-[(3RS)-3-hydroxy-1-undecinyl]-2-pyridyl-methyl}-tetrahydrofuran-2-one is obtained as oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05614634 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-c7081e8db41e4b5aa298f80153af9a59 |
| Source note | uspto-grants-1997_03 |