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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1872093Generated: October 25, 2026

Water → HCID 10987988, compound

https://huagongshe.com/reaction/1872093

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCyclohexanoneHCID 7967—
Reactant1-BenzocyclobutenecarbonitrileHCID 138838—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
SolventHexaneHCID 8058—
ProductHCID 10987988HCID 10987988—

Reaction Conditions

Temperature-78 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06107345
Source datasetuspto-grants-2000_08
ORD IDord-36fedf644c72436b8444abfa6eb68890
Source noteuspto-grants-2000_08