Solketal → 3-[(3-Methoxypyridin-2-yl)oxy]propane-1,2-diol

Participants

Reaction Steps

26.5 g of sodium hydride are added in the course of one hour to a mixture of 161 g of 3-methoxy-2-nitropyridine and 144 g of 2,2-dimethyl-5-hydroxymethyl-1,3-dioxolane in 1,000 ml of hexamethylphosphoric acid triamide, with stirring; by means of cooling, the temperature is kept at 0°-10° during the addition. The reaction mixture is then stirred for a further 5 hours with ice-cooling and then for 15 hours at room temperature. The reaction mixture is poured onto ice and extracted with diethyl ether. The organic extract is washed with a concentrated aqueous solution of sodium chloride, dried and evaporated. The residue is dissolved in 1,000 ml of ethanol, 100 ml of 2 N hydrochloric acid are added and the mixture is left to stand for 8 hours. After evaporating off the solvent, the residue is rendered alkaline with a concentrated solution of sodium hydroxide in water and extracted with ethyl acetate. Evaporating off the solvent yields a crude product from which crystalline 3-(3-methoxy-2-pyridyloxy)-1,2-propanediol with a melting point of 62°-65° is obtained on the addition of diethyl ether.

Provenance & Evidence