Dimethyl Sulfoxide → 4-(3-Methoxypropoxy)-2,3,5-trimethylpyridine 1-oxide

Temperatur

60 °C

4.5 g (0.05 mol) of methoxypropanol was dissolved in 45 ml of dimethyl sulfoxide to obtain a solution. 2.0 g of 60% sodium hydride was added to this solution at a room temperature in a nitrogen atmosphere. The obtained mixture was heated to 60° C. and stirred for one hour. After the completion of the reaction, a solution of 4.3 g (0.025 mol) of 4-chloro-2,3,5-trimethylpyridine 1-oxide in 15 ml of dimethyl sulfoxide was dropwise added to the reaction mixture at a room temperature. The obtained mixture was stirred at 60° C. for 5 hours, cooled and distilled to dryness to remove the solvent. 200 ml of water was added to the obtained residue. The obtained mixture was extracted with 150 ml of chloroform five times. The extract was dried over magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to obtain 4.27 g of the title compound as an oil.

1. customto obtain a solution
2. customAfter the completion of the reaction
3. stirringThe obtained mixture was stirred at 60° C. for 5 hours
4. temperaturecooled
5. distillationdistilled to dryness
6. customto remove the solvent
7. addition200 ml of water was added to the obtained residue
8. extractionThe obtained mixture was extracted with 150 ml of chloroform five times
9. dry with materialThe extract was dried over magnesium sulfate
10. filtrationfiltered
11. distillationThe filtrate was distilled
12. customto remove the solvent
13. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)

ORD-Eintrag

ord-1d58406a8b994aa7b63e9078ecd96c75

Quelldatensatz

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05840910