Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cyclohexanone | HCID 7967 | — |
| Reactant | 1-Benzocyclobutenecarbonitrile | HCID 138838 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 10987988 | HCID 10987988 | — |
Reaction Steps
Whilst maintaining the temperature at -78° C., 69 ml of 1.6M butyllithium in n-hexane are added to a solution of 12.9 g of 1-cyanobenzocyclobutane in 200 ml of tetrahydrofuran. After stirring for half an hour at that temperature, 15.5 ml of cyclohexanone are added and the reaction mixture is brought back to room temperature. After stirring for 3 hours at room temperature, the reaction mixture is hydrolysed at -10° C. with water. After extraction with diethyl ether, the organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo. The crystalline residue is recrystallised from isopropyl ether to yield 12.32 g of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06107345 |
|---|
| Source dataset | uspto-grants-2000_08 |
|---|
| ORD ID | ord-36fedf644c72436b8444abfa6eb68890 |
|---|
| Source note | uspto-grants-2000_08 |
|---|