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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2294097Generated: October 30, 2026

Acetic Acid → t-Butyl 4-[2-(2-cyano-3-methoxy-2-cyclopentenyl)ethyl]benzoate

https://huagongshe.com/reaction/2294097

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantDiisopropylethylamineHCID 81531—
Reactantt-Butyl 4-(2-(2-cyano-1-cyclopentanon-3-yl)ethyl]benzoateHCID 10470833—
SolventHexaneHCID 8058—
SolventAcetonitrile methanolHCID 21959252—
Productt-Butyl 4-[2-(2-cyano-3-methoxy-2-cyclopentenyl)ethyl]benzoateHCID 10359093—

Reaction Steps

t-Butyl 4-[2-(2-cyano-1-cyclopentanon-3-yl)-ethyl]benzoate (0.43 g, 1.37 mmol) prepared in the Preparative Example 105 and N,N-diisopropylethylamine (0.21 g, 1.64 mmol) were dissolved in a methanol/acetonitrile (1:5) mixture, followed by the addition of 3.2 g of a 10% by weight solution of trimethylsilyldlazomethane in hexane. The obtained mixture was stirred at room temperature for 2 hours, followed by the addition of a small amount of acetic acid. The mixture this obtained was stirred and distilled to remove the solvent. The residue was dissolved in diethyl ether, washed with diluted hydrochloric acid, dilute alkali ind an aqueous solution of common salt, dehydrated and concentrated to dryness. The residue was purified by silica gel column chromatography to give the objective compound. yield: 0.23 g

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05688800
Source datasetuspto-grants-1997_11
ORD IDord-e35299c00dfd46df91474b24e4abf21f
Source noteuspto-grants-1997_11