Dimethylformamide → HCID 86042697, Verbindung

HRID 1698395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698395
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.[Li]CCCC.CN([CH:25]=[O:26])C.[Cl-].[NH4+]>C1COCC1>[C:13]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:25]=[O:26])([CH3:16])([CH3:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 66671963(4-Bromo-2-tert-butylphenyl)diethylamineHCID 178418339Butyllithium

Produkt 1

HCID 86042697HCID 86042697, VerbindungAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3.6 g (13 mmol) of (4-bromo-2-tert-butylphenyl)-diethylamine are diluted in 100 ml of THF, under a stream of nitrogen. The medium is cooled to −78° C. and then 7.8 ml (20 mmol) of a 2.5M solution of nBuLi are added. After stirring for 45 minutes, 1.5 ml (20 mmol) of DMF are added and the solution is brought back to ambient temperature. After 15 minutes, the mixture is poured into a saturated solution of ammonium chloride and then extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate and then concentrated to dryness. 3.1 g of 3-tert-butyl-4-diethylaminobenzaldehyde are obtained in the form of a yellow oil (yield=100%).

Aufarbeitung

  1. customis brought back to ambient temperature
  2. waitAfter 15 minutes
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fb66f79ea88d45e2a2f2498efbdd22a7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163952B2

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