Water → 2-(Hydroxyphenyl-methyl)-6-methyl-pyridin-3-ol

HRID 228754

Reaktionsgleichung

Reaktionsgleichung von HRID 228754
[OH:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>O1CCCC1>[OH:10][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[C:5]([CH3:8])[N:4]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehydeHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 230783712-(Hydroxyphenyl-methyl)-6-methyl-pyridin-3-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Hydroxy-6-methyl-pyridine-2-carbaldehyde (350 mg) was dissolved in tetrahydrofuran (13 ml) to prepare a solution which was brought to −78° C. Phenylmagnesium bromide (7.4 ml) was slowly added dropwise thereto, and the mixture was stirred at room temperature for one hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give 2-(hydroxyphenyl-methyl)-6-methyl-pyridin-3-ol (553 mg, yield 100%).

Aufarbeitung

  1. customto prepare a solution which
  2. customwas brought to −78° C
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dbe8e2537f5a43f6abdac5e7d5c94209
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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