Reaktion #59882

Reaktionsgleichung

5,9-dioxaspiro[3.5]nonan-7-ol

sodium hydride

4-chloro-2,3-dimethylpyridine 1-oxide

→

title compound

Ausbeute 64.4%

4-(5,9-dioxaspiro[3.5]non-7-yloxy)-2,3-dimethylpyridine 1-oxide

Ausbeute 64.4%

Lösungsmittel

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   workup.STIRRINGthe mixture was stirred at 80° C. for 2 hours
3. 3
   EinengenThe reaction mixture was concentrated
4. 4
   workup.ADDITIONdimethylsulfoxide (30 ml) was added
5. 5
   workup.STIRRINGstirred at 80° C
6. 6
   workup.WAITAfter 12 hours
7. 7
   workup.ADDITIONwas added to the reaction mixture
8. 8
   workup.STIRRINGstirred at 80° C
9. 9
   workup.WAITAfter one hour
10. 10
    Einengenthe reaction mixture was concentrated
11. 11
    Sonstigethe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1)

Vorschrift

To a dimethyl formamide (30 ml) solution of the 5,9-dioxaspiro[3.5]nonan-7-ol (1.68 g, 11.7 mmol) obtained in the step (9e), sodium hydride, in oil (587 mg, 13.5 mmol as the content was regarded as 55%) was added at room temperature. The mixture was stirred at room temperature for 50 minutes. After 4-chloro-2,3-dimethylpyridine 1-oxide (1.84 g, 11.7 mmol) was added thereto, the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated and dimethylsulfoxide (30 ml) was added thereto and stirred at 80° C. After 12 hours, sodium hydride, in oil (587 mg, 13.5 mmol as the content was regarded as 55%) was added to the reaction mixture and stirred at 80° C. After one hour, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1) to obtain the title compound (2.00 g, yield: 64.4%) as a light yellow oil.

Quelle