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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1650600Generated: October 30, 2026

N,N,N',N'-Tetramethylethylenediamine → 4-Ethoxy-2,3-difluorobenzaldehyde

https://huagongshe.com/reaction/1650600

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,N,N',N'-TetramethylethylenediamineHCID 8037—
Reactant1-PiperidinecarboxaldehydeHCID 17429—
Reactant1-Ethoxy-2,3-DifluorobenzeneHCID 2782928—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
SolventHexaneHCID 8058—
Product4-Ethoxy-2,3-difluorobenzaldehydeHCID 14495625—

Reaction Conditions

Temperature-60 °C

Reaction Steps

125 ml of a solution of 0.2 mole of n-butyllithium in hexane is added, at -78° C., to a mixture of 0.2 mole of 2,3-difluorophenetole, 0.2 mole of tetramethylethylenediamine and 400 ml of tetrahydrofuran, and the mixture is stirred for 2 hours at -60° C. A mixture of 0.2 mole of n-formylpiperidine and 20 ml of tetrahydrofuran is added dropwise to this mixture. Warming to -20° C. and working up in the customary manner gives the aldehyde in the form of a colourless solid, melting point 70° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04925590
Source datasetuspto-grants-1990_05
ORD IDord-1be16e8dec7245dea897d064d38836e5
Source noteuspto-grants-1990_05