Diethyl Ether → alpha-[2-(Dimethoxymethyl)phenyl]-3-pyridinemethanol

HRID 1253042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253042
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:11][CH3:12])[O:9][CH3:10].O(CC)CC.C([Li])CCC.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1>CCCCCC>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:29]([C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1)[OH:30]

Komponenten

6

Edukt 4

HCID 3283Diethyl Ether2×HCID 103713-PyridinecarboxaldehydeHCID 111489431-Bromo-2-(dimethoxymethyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 14820335alpha-[2-(Dimethoxymethyl)phenyl]-3-pyridinemethanolAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred and cooled (-78° C.) mixture of 50 parts of 1-bromo-2-(dimethoxymethyl)benzene and 245 parts of 1,1'-oxybisethane were added dropwise 59 parts of a 1-butyllithium solution 2.5M in hexane. Upon complete addition, stirring was continued for 10 minutes at room temperature. A solution of 23.1 parts of 3-pyridinecarboxaldehyde in 42 parts of 1,1'-oxybisethane was added dropwise to the reaction mixture. Upon completion, the mixture was allowed to reach room temperature. The mixture was taken up in ice water and the product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated, yielding 56 parts (99.9%) of α-[2-(dimethoxymethyl)phenyl]-3-pyridinemethanol as a residue (intermediate 1).

Aufarbeitung

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. customto reach room temperature
  5. extractionthe product was extracted with 1,1'-oxybisethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2635f8c911bf4625b97ce2649a33c245
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04746671

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