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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1966838Generated: November 2, 2026

Diethyl Ether → [(3-Methylidenecyclobutoxy)methyl]benzene

https://huagongshe.com/reaction/1966838

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantSodium IodideHCID 5238—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant(3-(Benzyloxy)cyclobutyl)methyl methanesulfonateHCID 86647603—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
Product[(3-Methylidenecyclobutoxy)methyl]benzeneHCID 66732815—

Reaction Steps

Sodium iodide (0.45 gm, 3 mmol) and 1,8-diazabicyclo (5.4.0)undec-7-ene (0.304 gm, 2 mmol) were added to a stirred solution of [3-(benzyloxy)cyclobutyl]methyl methanesulfonate (0.27 gm, 1 mmol) (step b) in dimethoxyethane and the reaction mixture was refluxed for about 2 hours. It was allowed to come to room temperature and then was stirred with diethyl ether and water for about 10 minutes. The ether layer was separated and aqueous layer was washed with ether. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude compound was purified over silica gel.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08420666B2
Source datasetuspto-grants-2013_04
ORD IDord-b45a397891784fa3a91d9374d76d5f5d
Source noteuspto-grants-2013_04