1-Propanol → 2,3-Dimethyl-4-propoxypyridine 1-oxide

Participants

Reaction Conditions

Reaction Steps

To a solution prepared by diluting 8.6 g (2.0 eq.) of 60% sodium hydroxide with 200 mL of dimethylsulfoxide, 13.0 g of 1-propanol (2.0 eq.) was added, and the mixture was allowed to react for one hour at 60° C. The reaction liquid was cooled to 30° C., and then a solution containing 17.0 g of 4-chlor-2,3-dimethylpyridine-1-oxide dissolved in dimethylsulfoxide (70 mL) was added dropwise. The mixture was allowed to react for 3 hours at 40 to 50° C., and then was left to stand overnight at room temperature. 15 mL of water was added to the reaction liquid, and the mixture was concentrated, to obtain a residue in the form of a black paste. Subsequently, the residue was dissolved in 500 mL of water, and then the aqueous solution was extracted three times with 670 mL of chloroform. The extract was dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure, and the obtained residue was purified on a silica gel column, to obtain 20.3 g of 4-propoxy-2,3-dimethylpyridine-1-oxide.

Provenance & Evidence