Carbon Dioxide → Sodium tetrahydropyran-2-yloxyethanoate

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Reaction Steps

To a solution of tetrahydropyran-2-yloxyethanonitrile (6.0 g, 42.49 mmol) in ethanol (15 ml) was added aqueous sodium hydroxide solution (10M, 15 ml). Following the initial exothermic reaction the solution was heated under reflux for 1.5 hours, diluted with ethanol (30 ml) and the pH adjusted to 8 by the addition of carbon dioxide pellets. The resulting gelatinous suspension was diluted with acetonitrile (60 ml), filtered at 60° C. through diatomaceous earth and the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml). The crude product was purified by dissolution in warm isopropanol, filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C. to yield sodium tetrahydropyran-2-yloxyethanoate (6.24 g, 34.26 mmol) as a colorless powder, m.p. 198°-205° C.;

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