Nitrogen → 6-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

HRID 2064964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064964
N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[N:5]=1.[Li]CCCC.CN([CH:24]=[O:25])C.C([O-])(O)=O.[Na+]>CCOCC.CCCCCC>[CH3:15][C:10]1([C:6]2[N:5]=[C:4]([CH:24]=[O:25])[CH:9]=[CH:8][CH:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Komponenten

8

Edukt 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 121642822-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridineHCID 178418339Butyllithium

Produkt 1

HCID 860859206-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-6-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (2.21 g, 9.05 mmol) in Et2O (60.0 mL) at −78° C. was added dropwise n-BuLi (3.70 mL of a 2.5M solution in hexane, 9.25 mmol). The reaction mixture was then stirred at −78° C. for 30 min before DMF (0.85 mL, 11.00 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. 5% aq. NaHCO3 was added and the mixture was extracted three times with Et2O. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA to pure EA) gave the title compound as a pale yellow solid.

Aufarbeitung

  1. additionwas added dropwise
  2. extractionthe mixture was extracted three times with Et2O
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA to pure EA)

Quellen und Nachweise

ORD-Eintrag
ord-00c723701142415ca5fca446fe7c609b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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