5-phenylpyridine-2-carboxylic Acid → (5-Phenylpyridin-2-yl)methanol

HRID 363188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363188
[C:1]1([C:7]2[CH:8]=[N:9][C:10]([C:13](O)=[O:14])=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2[CH:8]=[N:9][C:10]([CH2:13][OH:14])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 27628705-phenylpyridine-2-carboxylic AcidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 54044516(5-Phenylpyridin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-phenyl-6-carboxypyridine (1.05 g, 5.27 mmol) in tetrahydrofuran (25 mL) at 0° C. was added 1.0M lithium aluminum hydride in tetrahydrofuran (10.0 mL, 10.0 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 6 hours, cooled to 0° C., and quenched by dropwise addition of water (0.50 mL), 4N aq. NaOH (0.50 mL), and water (1.5 mL). The reaction was filtered through a pad of Celite and the filtrate evaporated in vacuo. The residue was chromatographed (silica gel, 0-5% MeOH in CH2Cl2) to afford the title compound.

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of water (0.50 mL), 4N aq. NaOH (0.50 mL), and water (1.5 mL)
  3. filtrationThe reaction was filtered through a pad of Celite
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was chromatographed (silica gel, 0-5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-cd2bbb6f6ed6467b95475b20fc565e31
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872136

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