HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → HCID 67452252, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 2,6-Difluoropyridine | HCID 73934 | — |
| Reactant | Cyanocyclobutane | HCID 78148 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67452252 | HCID 67452252 | 64.7% |
Reaction Steps
To a 0° C. solution of 2,6-difluoropyridine (5.0 g, 43 mmol), cyclobutanecarbonitrile (3.5 g, 43 mmol), and toluene (100 mL) was added sodium hexamethyldisilazide (NaHMDS, 2.0 M in THF, 24 mL, 47 mmol). The resulting mixture was warmed to rt and stirred for 2 h. The mixture was then diluted with EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, concentrated, and purified using silica gel chromatography to provide the desired product (4.9 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133123B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-ef27d146d5854bec9a84ff56ed692c77 |
| Source note | uspto-grants-2015_09 |