Acetic Acid → (2-Chloro-6-methylpyridin-4-yl)methanol

HRID 279571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279571
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([C:14](OCC)=[O:15])[CH:11]=[C:10]([CH3:19])[N:9]=1.C(O)(=O)C>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([CH3:19])[N:9]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 21226445Aluminium lithium hydrideHCID 22625009Ethyl 2-Chloro-6-methylisonicotinate

Produkt 1

HCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanolAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium aluminium hydride (350 mg, 9.26 mmol) was added in portions to a solution of ethyl 2-chloro-6-methyl-4-pyridinecarboxylate (1.85 g, 9.26 mmol) in THF (40 ml) cooled at 0° C. The mixture was stirred for 15 minutes at 0° C. and acetic acid (2 ml) was added. The mixture was partitioned between ethyl acetate and water and the aqueous layer was adjusted to pH7.5 with 5 % aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (35/65) to give 2-chloro-4-hydroxymethyl-6-methylpyridine (1.28 g, 88%).

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate/petroleum ether (35/65)

Quellen und Nachweise

ORD-Eintrag
ord-b19dabf2b231478dbf43d5eb1d685101
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362336B1

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