Sodium Hydroxide → (6-Phenylpyridin-3-yl)methanol

HRID 914456

Reaktionsgleichung

Reaktionsgleichung von HRID 914456
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:13][CH:12]=1)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[C:17]1([C:14]2[N:13]=[CH:12][C:11]([CH2:10][OH:9])=[CH:16][CH:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 11096332Ethyl 6-phenylnicotinateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 22254216(6-Phenylpyridin-3-yl)methanolAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (3.50 g) was suspended in tetrahydrofuran (200 mL), 6-phenylnicotinic acid ethyl ester (21.0 g) synthesized in Reference Example 19 was added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was ice-cooled, water (5 mL) and aqueous sodium hydroxide solution (1 mol/L, 10 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 1 hr. Anhydrous sodium sulfate was added to the reaction mixture, the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 1:3) to give the title compound (17.0 g) as a colorless oil.

Aufarbeitung

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooled
  4. temperatureAfter warming to room temperature
  5. stirringthe mixture was stirred for 1 hr
  6. filtrationthe mixture was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-b291f32fafb14751874c9cbdacd2d01c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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