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Water → 4-(Dibenzylamino)benzaldehyde

HRID 1058647
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1058647
Br[C:2]1[CH:22]=[CH:21][C:5]([N:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:36]=[O:37].O>O1CCCC1>[CH2:7]([N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5]1[CH:21]=[CH:22][C:2]([CH:36]=[O:37])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 285423n,n-Dibenzyl-4-bromoanilineHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 150959344-(Dibenzylamino)benzaldehydeAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In an argon atmosphere, the obtained 4-bromo-N,N-dibenzylaniline (425 mg, 1.21 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled to −78° C. A 1.6 M n-butyl lithium hexane solution (1.1 mL, 1.8 mmol) was added thereto, and, 5 minutes thereafter, dimethylformamide (0.186 mL, 2.4 mmol) was further added thereto, followed by stirring for 5 minutes. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (9:1 hexane/ethyl acetate) to obtain 4-(dibenzylamino)benzaldehyde (192 mg, 53%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (9:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1903227c4a5744f886a98ae7ef0c5223
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06518268B1

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