Potassium Carbonate → HCID 86653794, Verbindung

HRID 85132

Reaktionsgleichung

Reaktionsgleichung von HRID 85132
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehydeHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

Produkt 1

HCID 86653794HCID 86653794, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 2-bromo-5-hydroxybenzaldehyde (62; 5 g, 0.025 mol) in DMF (100 ml) was added (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (63; 4.87 g, 0.032 mol) and K2CO3 (7.0 g, 0.05 mol). The resulting reaction mixture was stirred at 150° C. for 10 h, cooled to room temperature, diluted with water, and then extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1 to afford the desired product, namely (S)-2-bromo-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde 64 (4.1 g, 56%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1

Quellen und Nachweise

ORD-Eintrag
ord-7cb895ee291041ef807b9d856cc72837
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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