Dimethylformamide → 5-(Dimethoxymethyl)picolinaldehyde

HRID 885837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885837
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:16][CH3:17])[O:14][CH3:15])=[CH:9][N:8]=1.CN([CH:21]=[O:22])C>CCCCCC.C1COCC1.O>[CH3:15][O:14][CH:13]([O:16][CH3:17])[C:10]1[CH:11]=[CH:12][C:7]([CH:21]=[O:22])=[N:8][CH:9]=1

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 64252132-Bromo-5-(dimethoxymethyl)pyridineHCID 178418339Butyllithium

Produkt 1

HCID 184267805-(Dimethoxymethyl)picolinaldehydeAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A solution of 2.5 M BuLi in hexane (7.6 ml) was added drop-wise, under a N2 atmosphere, to a solution of 2-bromo-5-dimethoxymethyl-pyridine (3.66 g, 15.84 mmol) in THF (60 ml) at −70° C. After 15 minutes, DMF (1.82 ml, 23.5 mmol) was added drop-wise and the mixture was stirred for 30 minutes at −70° C. and then allowed to reach room temperature. The reaction was diluted with H2O and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated to dryness in vacuo. The crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3) to obtain 1.54 g of 5-dimethoxymethyl-pyridine-2-carbaldehyde as a yellow oil.

Aufarbeitung

  1. customat −70° C
  2. customto reach room temperature
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customThe crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-dfebf1fb641e4b699ce82772e6849100
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242175B2

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