Dimethylformamide → 5-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)-2-methoxybenzaldehyde

HRID 850435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 850435
Br[C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1C[O:20][CH2:19]C1.C([Li])CCC.CN(C=O)C>O.CCCCCC>[CH3:15][C:13]1([CH3:16])[CH2:12][O:11][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([CH:3]=2)[CH:19]=[O:20])=[N:14]1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 193633822-(3-Bromo-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418339Butyllithium

Produkt 1

HCID 193633795-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)-2-methoxybenzaldehydeAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-(3-Bromo-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (2.1 g, 7.4 mmol) and THF (15 ml) were mixed, and this solution was cooled to -78° C. A hexane solution (1.6M, 4.75 ml) of n-butyllithium (7.6 mmol) was added, and the mixture was stirred for 2 hours. DMF (1.16 ml, 15 mmol) was added and the mixture was stirred for 20 minutes. Water (20 ml) was added to stop the reaction. The aqueous layer was extracted twice with ethyl acetate (20 ml). The organic layers were combined, and washed with saturated brine (30 ml). This solution was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/3) to give 5-(4,4-dimethyl-4,5-dihydrooxazole-2-yl)-2-methoxybenzaldehyde (0.71 g, 41%) as colorless transparent crystals.

Aufarbeitung

  1. stirringthe mixture was stirred for 20 minutes
  2. customthe reaction
  3. extractionThe aqueous layer was extracted twice with ethyl acetate (20 ml)
  4. washwashed with saturated brine (30 ml)
  5. dry with materialThis solution was dried over anhydrous magnesium sulfate
  6. filtrationthe drying agent was filtered off
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/3)

Quellen und Nachweise

ORD-Eintrag
ord-3e10c1049cdb44eab19e34cb31cf7c73
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017919

Notizen zur Reaktion

Wird geladen…