Tetrahydrofuran → (6-Methylpyridin-3-yl)methanol

HRID 392467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392467
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C:8]1[C:13]([C:14]([O:16]C)=O)=[CH:12][N:11]=[CH:10][CH:9]=1.O1CCC[CH2:19]1>O.[OH-].[Na+]>[CH3:19][C:10]1[N:11]=[CH:12][C:13]([CH2:14][OH:16])=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 10877301methyl 4-methylnicotinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 11228788(6-Methylpyridin-3-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 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 4-methylnicotinate (15, 1.0 g, 6.6 mmol) in anhydrous tetrahydrofuran (5 mL). After 1.5 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) 8.34 (s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.12 (d, J=7.9 Hz, 1H), 4.65 (s, 2H), 4.18-4.10 (bs, 1H), 2.51 (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-87ccb7c706924bf981a55c4ce907bef4
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800651B2

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