HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Hexynenitrile → HCID 178510972, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Hexynenitrile | HCID 139852 | — |
| Reactant | HCID 178522917 | HCID 178522917 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | HCID 178510972 | HCID 178510972 | — |
Reaction Steps
To a solution of the title compound of Example 5 (0.35 g), CuI (0.042 g), and Pd(PPh3)2Cl2 (0.012 g) in 10 mL diethylamine is added 5-hexynenitrile (0.085 mL). The reaction is stirred overnight. The reaction is then partitioned between ethyl acetate and water. The organic layer is washed twice with water, dried over MgSO4, filtered, and adsorbed onto silica. A Biotage Flash 40S (eluent 3% MeOH:CH2Cl2) affords the desired product. The product is recrystallized from CH2Cl2 --MeOH/hexanes. A second crop of crystals is obtained by concentration of the filtrate. The total yield of the title compound is 0.21 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06093732 |
| Source dataset | uspto-grants-2000_07 |
| ORD ID | ord-8e626f8a57e64fa7a16c7f6c41c5e46d |
| Source note | uspto-grants-2000_07 |