HuagongsheHuagongshe Chemistry Print Report · For research reference only
Monobenzone → 3-(4-Benzyloxy-phenoxy)-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Monobenzone | HCID 7638 | — |
| Reactant | Diglyme | HCID 8150 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Iodopyridine | HCID 70714 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-(4-Benzyloxy-phenoxy)-pyridine | HCID 68999185 | 26.2% |
Reaction Steps
To a solution of p-benzyloxyphenol (550 mg, 2.754 mmol), Cs2CO3 (1.795 g, 5.509 mmol), 3-iodo pyridine (850 mg, 4.14 mmol) in anhydrous dioxane (15 ml) under N2 was added diglyme (38.42 mg, 0.275 mmol). After stirring for 10 min, CuI (19.38 mg, 0.102 mmol) was added and the reaction mixture was kept in a shaker at 85° C. overnight. The mixture was poured into EtOAc and water, the organic layer was dried over Na2SO4, and concentrated. Silica gel flash chromatography using EtOAc/Hexane gave the title compound (200 mg, 17%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08598359B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-f25cd57d69554f58ab2905fc224187d6 |
| Source note | uspto-grants-2013_12 |