Acetic Anhydride → 2-Hydroxymethyl-4-propoxypyridine

Beteiligte Stoffe

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Reaktionsschritte

A mixture of 2-methyl-4-propoxypyridine-1-oxide (8.6 g), acetic anhydride (8.6 ml) and concentrated sulfuric acid (two drops) was heated at 100° C. for five minutes, to which were added ice-water and an excess amount of sodium carbonate. The mixture was subjected to extraction with chloroform. The extract was dried with sodium sulfate, and the solvent was evaporated off. The residue was chromatographed on a column of silica-gel (200 g), which was eluted with carbon tetrachloride-acetone (5:3). The eluate was subjected to evaporation to remove the solvent. The residue (7.3 g) was dissolved in a solution of potassium hydroxide (2.8 g) in a mixture of water (3 ml) and methanol (60 ml). The resultant solution was stirred at room temperature for 15 minutes, to which were added ice-water and an excess amount of sodium carbonate. The mixture was subjected to extraction with ethyl acetate. The extract was dried with sodium sulfate, then the solvent was evaporated off. The residue was chromatographed on a column of silica-gel (150 g), which was eluted with 5% methanol-chloroform to yield 2-hydroxymethyl-4-propoxypyridine (4.4 g) as an oily substance.

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