Sodium hydride → 4-((2-Methoxy-1,3-dioxan-5-yl)methoxy)-2,3-dimethylpyridine 1-oxide

HRID 31593

Reaktionsgleichung

Reaktionsgleichung von HRID 31593
[CH3:1][O:2][CH:3]1[O:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][O:4]1.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][N+:17]([O-:20])=[C:16]([CH3:21])[C:15]=1[CH3:22]>CS(C)=O>[CH3:1][O:2][CH:3]1[O:8][CH2:7][CH:6]([CH2:9][O:10][C:14]2[CH:19]=[CH:18][N+:17]([O-:20])=[C:16]([CH3:21])[C:15]=2[CH3:22])[CH2:5][O:4]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumHCID 59792360(2-Methoxy-1,3-dioxan-5-yl)methanol

Produkt 1

HCID 597925894-((2-Methoxy-1,3-dioxan-5-yl)methoxy)-2,3-dimethylpyridine 1-oxideAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a dimethylsulfoxide (10 ml) solution of the (2-methoxy-1,3-dioxan-5-yl)methanol (2.0 g, 13.5 mmol) obtained in the same manner of step (6a), sodium hydride, in oil (770 mg, 14.9 mmol as the content was regarded as 55%) was added at room temperature. To the mixture, 4-chloro-2,3-dimethylpyridine 1-oxide (2.13 g, 13.5 mmol) was added and the mixture was stirred at 60° C. for 2.5 hours. After the reaction mixture was cooled to room temperature, it was concentrated. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol) to obtain the title compound (1.8 g, 49.5% yield), which was a cis and trans (1:1) mixture, as a yellow oil.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8999a2a805a14ab1ac0958124306d33d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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