Reaktion #1787

ord-4b7921c79135478487a5a927dd9e4a45

Reaktionsgleichung

CCOC(=O)c1c(C)ccnc1C
2,4-dimethyl-3-carboethoxypyridine
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
Cc1ccnc(C)c1CO
2,4-dimethyl-3-hydroxymethylpyridine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthen cooled to 0° C.
  2. 2
    Sonstigequenched with EtOAc (2.5 mL)
  3. 3
    FiltrationThe solution was filtered
  4. 4
    Sonstigethe solvent removed under reduced pressure

Vorschrift

The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (2.5 mL), then H2O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726172uspto-grants-1998_03