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

HRID 1650600Notes

Reaction equation

C([Li])CCC.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[O:14][CH2:15][CH3:16].CN(C)CCN(C)C.C1CCN([CH:31]=[O:32])CC1>CCCCCC.O1CCCC1>[CH2:15]([O:14][C:8]1[CH:9]=[CH:10][C:11]([CH:31]=[O:32])=[C:12]([F:13])[C:7]=1[F:6])[CH3:16]

Participants

Conditions

Temperature: -60 °C

Procedure

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.

Workup

additionis added dropwise to this mixture
temperatureWarming to -20° C.

Sources & evidence

ORD record: ord-1be16e8dec7245dea897d064d38836e5
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04925590

Reaction notes

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