Sodium hydride → 5-(t-Butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine

HRID 1940382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940382
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CN(C=O)C.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 4194905-Hydroxy-2-hydroxymethylpyridine

Produkt 1

HCID 214660515-(t-Butoxycarbonylmethyl)oxy-2-hydroxymethylpyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The solution of 5-hydroxy-2-hydroxymethylpyridine (5.0 g) in DMF (10 ml) was titrated under ice-cooling in the suspension of sodium hydride (60% purity, 1.6 g) in DMF (10 ml). After 10 minutes, the mixture was heated to room temperature and stirred for 15 minutes. After t-butyl bromoacetate (6 ml) was added to the mixture under ice-cooling, the resulting mixture was stirred under ice-cooling for 10 minutes and at room temperature for 45 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and brine and dried over anhydrous magnesium sulfate. After the solvents were removed by distillation, the residue was purified by column chromatography on silica gel with an eluent system of chloroform→chloroform:methanol=50:1 to give 8.16 g of 5-(t-butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine (yield, 85%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred under ice-
  3. temperaturecooling for 10 minutes and at room temperature for 45 minutes
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvents were removed by distillation
  7. customthe residue was purified by column chromatography on silica gel with an eluent system of chloroform→chloroform

Quellen und Nachweise

ORD-Eintrag
ord-0e7f45ad76aa42c3b5ebd1d5d8f5dd2e
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698692

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