Carbon Dioxide → Sodium tetrahydropyran-2-yloxyethanoate

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.;

1. customexothermic reaction the solution
2. temperaturewas heated
3. temperatureunder reflux for 1.5 hours
4. filtrationfiltered at 60° C. through diatomaceous earth
5. extractionthe insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml)
6. customThe crude product was purified by dissolution in warm isopropanol
7. filtrationfiltration at 0° C.
8. customthrough diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C.

ORD 기록

ord-56f6f1a3df2341c1b4970df530132daa

출처 데이터셋

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05246950