Sodium ethoxide → 2-(Ethoxymethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

4-Benzyl-2-(p-toluenesulfonyloxymethyl)morpholine hydrochloride [cf. Reference Example 11-(1)] (3 g) and sodium ethoxide (2 g) are added to ethanol (150 ml), and the mixture is stirred at 70° C. for 24 hours. The reaction mixture is concentrated under reduced pressure, and to the residue is added saturated aqueous sodium hydrogen carbonate, and the mixture is extracted with ethyl acetate. The extract is washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (eluted by chloroform-methanol=40:1) and further subjected to bulb-to-bulb distillation (at 162° C., 0.4 mmHg) to give the title compound (0.9 g) as colorless liquid.

Provenance & Evidence