Sodium hydride → 4-(((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-2,3-dimethylpyridine 1-oxide

HRID 31620

Reaktionsgleichung

Reaktionsgleichung von HRID 31620
[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][N+:16]([O-:19])=[C:15]([CH3:20])[C:14]=1[CH3:21]>CS(C)=O>[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][O:8][C:13]2[CH:18]=[CH:17][N+:16]([O-:19])=[C:15]([CH3:20])[C:14]=2[CH3:21])[CH2:4][O:3]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 736056(R)-SolketalHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Produkt 1

HCID 597925474-(((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-2,3-dimethylpyridine 1-oxideAusbeute 136 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a dimethylsulfoxide (48 ml) solution of the ((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (4.87 g, 39.7 mmol), sodium hydride, in oil (1.73 g, 39.6 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (4.8 g, 30.5 mmol) was added, the mixture was stirred at 60° C. for 2 hours. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol) to obtain the title compound (10.5 g, yield: 136%) as a yellow oil.

Aufarbeitung

  1. additionwas added at room temperature
  2. temperatureAfter cooled to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-de375aaca8f74071bd9828ec77c4050a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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