Methyl 4-methoxy-3,5-dimethylpicolinate → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

HRID 52435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52435
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]([CH3:20])=[CH:13][N:12]=1)=O>C1COCC1>[OH:8][CH2:9][C:11]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]([CH3:20])=[CH:13][N:12]=1

Komponenten

4

Edukt 2

HCID 10313519Methyl 4-methoxy-3,5-dimethylpicolinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridineAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminum hydride (0.94 g, 25.4 mmol) was dissolved in 100 ml of absolute THF and added in a dropwise manner to a stirred solution of compound 8 (2.5 g, 12.82 mmol) in 20 ml of THF at 0° C. The mixture was stirred at 0° C. for 2 hr. Excess LiAlH4 was then destroyed with ethyl acetate. The combined organic phases were dried, filtered, and evaporated in vacuo to give compound 9 (1.1 g, 50% yield). It gave same analytic data as those of an authentic sample.

Aufarbeitung

  1. customExcess LiAlH4 was then destroyed with ethyl acetate
  2. customThe combined organic phases were dried
  3. filtrationfiltered
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a4da9fc57b8547998211fad2d1f0b5b9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616713

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