Methyl 2-methylnicotinate → (2-Methylpyridin-3-yl)methanol

HRID 392466

Reaktionsgleichung

Reaktionsgleichung von HRID 392466
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:17]=[CH:16][CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11]>O1CCCC1.O.[OH-].[Na+]>[CH3:7][C:8]1[C:9]([CH2:10][OH:11])=[CH:14][CH:15]=[CH:16][N:17]=1

Komponenten

6

Edukt 2

HCID 7015327Methyl 2-methylnicotinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 302564(2-Methylpyridin-3-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a slurry of lithium aluminum hydride (500 mg, 13.2 mmol) in anhydrous tetrahydrofuran (45 mL) at 0° C. under nitrogen was added dropwise a solution of methyl 2-methylnicotinate (17, 1.0 g, 6.6 mmol) in anhydrous tetrahydrofuran (5 mL). After 1 h the suspension was diluted with water (1 mL) and 6 N NaOH solution (5 mL). The precipitate was removed by vacuum filtration and the filtrate was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide the title compound as a light yellow oil: 1H NMR (300 MHz) 8.37 (d, J=4.9 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.14 (dd, J=7.6 Hz, 4.9 Hz, 1H), 4.72 (s, 2H), 2.95-2.74 (bs, 1H), 2.53 (s, 3H) ppm.

Aufarbeitung

  1. customThe precipitate was removed by vacuum filtration
  2. dry with materialthe filtrate was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7dde4db91cc844f691554aad9e6c8b40
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800651B2

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